4595-59-9

Basic information

• Product Name: 5-Bromopyrimidine
• Synonyms: 5-bromo-pyrimidin;PYRIMIDINE, 2-BROMO-;PYRIMIDINE, 5-BROMO-;5-BROMOPYRIMIDINE;5-Bromopyrimidine,98%;Pyrimidine,5-bromo-(6CI,7CI,8CI,9CI);5-BROMOPYRIMIDINE, 99% MIN;5-BROMOPYRIMIDINE 0.98
• CAS NO: 4595-59-9
• Molecular Formula: C₄H₃BrN₂
• Molecular Weight: 158.98
• EINECS: 224-992-1
• Product Categories: HALIDE;Pyridines, Pyrimidines, Purines and Pteredines;Halides;Pyrazines, Pyrimidines & Pyridazines;Aromatics Compounds;Aromatics;Heterocycles;Pyrazines, Pyrimidines & Pyridazines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrimidines;PyrimidinesHeterocyclic Building Blocks;Pyrimidine;Heterocycle-Pyrimidine series
• Mol File: 4595-59-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 69 °C
• Boiling Point: 168°C(lit.)
• Flash Point: 75.623 °C
• Appearance: Yellow to beige-brown/Crystalline Powder or Chunks
• Density: 1.6448 (rough estimate)
• Vapor Pressure: 0.437mmHg at 25°C
• Refractive Index: 1.5260 (estimate)
• Storage Temp.: Keep Cold
• Solubility: Soluble in chloroform.
• PKA: 1.40±0.10(Predicted)
• BRN: 107326
• CAS DataBase Reference: 5-Bromopyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromopyrimidine(4595-59-9)
• EPA Substance Registry System: 5-Bromopyrimidine(4595-59-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: T
• HazardClass: IRRITANT, KEEP COLD
• Hazardous Substances Data: 4595-59-9(Hazardous Substances Data)

Usage

Chemical Properties

yellow solid crystalline, insoluble in water, soluble in organic solvents such as benzene and toluene.

Uses

Different sources of media describe the Uses of 4595-59-9 differently. You can refer to the following data:
1. 5-Bromopyrimidine was used in the synthesis of N-heteroaryl substituted 9-arylcarbazolyl derivatives via palladium-catalyzed aerobic and ligand-free Suzuki reaction, (5-(phenylethynyl)pyrimidine) via microwave assisted organic synthesis (MAOS) Sonogashira protocol.
2. 5-Bromopyrimidine was used in the synthesis of:N-heteroaryl substituted 9-arylcarbazolyl derivatives via palladium-catalyzed aerobic and ligand-free Suzuki reaction(5-(phenylethynyl)pyrimidine) via microwave assisted organic synthesis (MAOS) Sonogashira protocolIntermediate for the synthesis of plant growth regulator flurprimidol

Application

5-Bromopyrimidine is a compound useful in organic synthesis.

Preparation

5-Bromopyrimidine is prepared by reacting dibromodifuranone with formamide in the presence of B2O2 catalyst at 180-185°C to obtain the product.

General Description

Rapid nucleophilic displacement reactions of 5-bromopyrimidine with nucleophiles under microwave irradiation has been studied. 5-Bromopyrimidine undergoes direct metallation with lithuium diisopropylamide to yield 4-lithio-5-bromopyrimidine.

InChI:InChI=1/C4H3BrN2/c5-4-1-6-3-7-2-4/h1-3H

Synthetic route

mucobromic acid (766-38-1) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → 5-bromopyrimidine (4595-59-9)

Conditions	Yield
With boron trioxide In methanol at 180 - 185℃; for 15h;	48%

5-bromo-4-(1H-indol-3-yl)-3,4-dihydropyrimidin-1-ium tetrafluoroborate → 5-bromopyrimidine (4595-59-9) + indole (120-72-9) + 3-(5-bromopyrimidin-4-yl)-1H-indole (1433688-83-5) + 3-(pyrimidin-4-yl)-1H-indole (57826-98-9)

Conditions	Yield
With potassium hydroxide; potassium hexacyanoferrate(III) In water at 20℃; for 2h;	A 8 %Chromat. B 12 %Chromat. C 40% D 17 %Chromat.

5-bromo-4-(1-ethyl-1H-indol-3-yl)-3,4-dihydropyrimidin-1-ium tetrafluoroborate → 5-bromopyrimidine (4595-59-9) + N-Ethylindole (10604-59-8) + 3-(5-Bromopyrimidin-4-yl)-1-ethyl-1H-indole (1433688-86-8)

Conditions	Yield
With potassium hydroxide; potassium hexacyanoferrate(III) In water at 20℃; for 2h;	A 9 %Chromat. B 25 %Chromat. C 40%

5-bromo-4-(1H-indol-3-yl)-3,4-dihydropyrimidin-1-ium tetrafluoroborate → 5-bromopyrimidine (4595-59-9) + indole (120-72-9) + 3-(pyrimidin-4-yl)-1H-indole (57826-98-9)

Conditions	Yield
With piperidine In water at 20℃; for 2h;	A 22 %Chromat. B 35 %Chromat. C 23%

5-bromo-2-pyrimidinecarboxylic acid (37131-87-6) → 5-bromopyrimidine (4595-59-9)

Conditions	Yield
at 250℃;

pyrimidine hydrochloride (30680-61-6) → 5-bromopyrimidine (4595-59-9)

Conditions	Yield
With bromine at 160℃;
With bromine; sodium carbonate In water; nitrobenzene; benzene

bromine (7726-95-6) + pyrimidine hydrochloride (30680-61-6) → 5-bromopyrimidine (4595-59-9)

2,4-dichloro-5-bromopyrimidine (36082-50-5) + 4-sulphanilamide → 5-bromopyrimidine (4595-59-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In diethyl ether; butan-1-ol

5-bromo-2-iodopyrimidine (183438-24-6) + 5-bromo-2-(5-bromothiophen-2-yl)pyridine (136902-53-9) → 5-bromopyrimidine (4595-59-9) + 5-bromo-2-(thiophen-2-yl)pyridine (91891-74-6)

Conditions	Yield
Stage #1: 5-bromo-2-iodopyrimidine; 5-bromo-2-(5-bromothiophen-2-yl)pyridine With isopropylmagnesium chloride In tetrahydrofuran Stage #2: Hydrolysis;

5-bromopyrimidine (4595-59-9) + ethanol (64-17-5) + carbon monoxide (201230-82-2) → ethyl pyrimidine-5-carboxylate (40929-50-8)

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride at 100℃; under 5171.5 Torr;	100%

5-bromopyrimidine (4595-59-9) + phenylboronic acid (98-80-6) → 5-phenylpyrimidine (34771-45-4)

Conditions	Yield
With caesium carbonate; palladium diacetate In N,N-dimethyl-formamide at 80℃; for 6h; Suzuki-Miyaura cross-coupling reaction;	100%
With potassium carbonate In ethanol; water at 30℃; for 1h; Suzuki-Miyaura Coupling;	100%
With N,N,N′,N′-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine; potassium carbonate; palladium dichloride In 1,4-dioxane; N,N-dimethyl-formamide at 90℃; for 6h; Suzuki coupling; Inert atmosphere;	99%

5-bromopyrimidine (4595-59-9) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → tert-butyl 4-(pyrimidin-5-yl)piperazine-1-carboxylate (634468-96-5)

Conditions	Yield
Stage #1: 5-bromopyrimidine; 1-t-Butoxycarbonylpiperazine With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In xylene at 50℃; Stage #2: With macroporous polymer-supported isocyanate In xylene at 50℃; for 24h;	100%
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 90℃; for 12h;	58.7%
Stage #1: 5-bromopyrimidine; 1-t-Butoxycarbonylpiperazine With sodium t-butanolate In toluene for 0.25h; Heating / reflux; Stage #2: palladium diacetate; tri-tert-butyl phosphine for 32h; Heating / reflux;
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene for 16h; Reflux; Inert atmosphere;

5-bromopyrimidine (4595-59-9) + benzofuran-2-boronic acid (98437-24-2) → 5-(benzofuran-2-yl)pyrimidine

Conditions	Yield
With sodium phosphate dodecahydrate; palladium 10% on activated carbon In isopropyl alcohol at 80℃; for 12h; hetero-Suzuki-Miyaura cross-coupling; Inert atmosphere;	100%
With sodium phosphate; palladium on activated charcoal In isopropyl alcohol at 80℃; for 3h; Suzuki-Miyaura coupling reaction;	95%
With C43H37ClFeNiP2*C4H8O; potassium carbonate In tetrahydrofuran; acetonitrile at 50℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere;	89%
With tetra-butylammonium acetate; Pd EnCat-30TM In ethanol at 120℃; for 0.166667h; Suzuki cross-coupling; microwave irradiation;	72%

5-bromopyrimidine (4595-59-9) + 1-Naphthylboronic acid (13922-41-3) → 5-(naphthalen-1-yl)pyrimidine

Conditions	Yield
With potassium phosphate monohydrate; C66H84O10P2Pd In water; toluene at 45℃; for 4.5h; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere;	100%
With (3-phenylallyl)(chloro)-[1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene]palladium(II); potassium carbonate In ethanol at 40℃; for 4h; Suzuki-Miyaura Coupling; Green chemistry;	99%
With potassium carbonate In water; toluene at 90℃; for 0.5h; Suzuki-Miyaura Coupling;	97%

5-bromopyrimidine (4595-59-9) + (4,4-difluoro-piperidin-1-yl)-[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-methanone (872030-12-1) → (4,4-difluoro-piperidin-1-yl)-[5-(1-isopropyl-piperidin-4-yloxy)-1-pyrimidin-5-yl-1H-indol-2-yl]-methanone

Conditions	Yield
Stage #1: 5-bromopyrimidine; (4,4-difluoro-piperidin-1-yl)-[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-methanone With potassium phosphate; (S,S)-1,2-diaminocyclohexane; copper(l) iodide In 1,4-dioxane for 72h; Heating / reflux; Stage #2: With potassium carbonate In 1,4-dioxane for 24h; Heating / reflux;	100%

5-bromopyrimidine (4595-59-9) + 2-formylbenzene boronic acid (40138-16-7) → 2-(pyrimidin-5-yl)benzaldehyde (640769-71-7)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water Suzuki coupling; Heating;	100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; 1,2-dimethoxyethane; water at 80℃;	70%
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 150℃; for 0.0833333h; Microwave irradiation;
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 150℃; for 0.0833333h; Sealed tube; Microwave irradiation;	220 mg

5-bromopyrimidine (4595-59-9) + trifluoroethylamine (753-90-2) → C6H6F3N3

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); 5-(di(adamantan-1-yl)phosphino)-1′,3′,5′-triphenyl-1′H-1,4′-bipyrazole; potassium phenolate In 1,4-dioxane at 100℃; for 6h; Sealed tube; Inert atmosphere;	100%

5-bromopyrimidine (4595-59-9) + 2-methoxypyridin-3-yl-boronic acid (163105-90-6) → 3-(pyrimidin-5-yl)thiophene (58759-02-7)

Conditions	Yield
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In tert-Amyl alcohol for 12h; Solvent; Suzuki-Miyaura Coupling; Heating;	100%

5-bromopyrimidine (4595-59-9) + tert-butyl 2-(3-carbamoyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazol-1-yl)acetate → tert-butyl 2-(3-carbamoyl-6-(pyrimidin-5-yl)-1H-indazol-1-yl)acetate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	100%

5-bromopyrimidine (4595-59-9) + 1-butyn-4-ol (927-74-2) → 4-(5-pyrimidinyl)-3-butyn-1-ol (88940-56-1)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In dichloromethane at 50℃; for 15h; Sonogashira Cross-Coupling; Inert atmosphere;	99%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; lithium chloride In water for 2h; Sonogashira coupling; Reflux; Inert atmosphere;	83%
With copper(l) iodide; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)); (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 100℃; for 20h;	75%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In dichloromethane for 2h; Heating;
With tetrakis(triphenylphosphine) palladium(0); copper(l) chloride; lithium chloride at 80℃; Castro-Stevens reaction;

5-bromopyrimidine (4595-59-9) + benzylamine (100-46-9) → N-benzyl-5-aminopyrimidine (104479-78-9)

Conditions	Yield
With cesium acetate; copper In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere;	99%
With dibenzylphosphoramidous acid 1,1'-binaphthyl-2,2'-diyl ester; caesium carbonate; copper(I) bromide In N,N-dimethyl-formamide at 90℃; for 36h;	96%
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; palladium diacetate; potassium carbonate In tert-butyl alcohol at 110℃; for 24h; Catalytic behavior; Reagent/catalyst; Buchwald-Hartwig Coupling; Inert atmosphere;	92%

5-bromopyrimidine (4595-59-9) + potassium phenyltrifluoborate → 5-phenylpyrimidine (34771-45-4)

Conditions	Yield
With water; palladium diacetate; sodium carbonate at 80℃; for 4h; Suzuki Coupling; Green chemistry;	99%
With palladium diacetate; sodium carbonate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In water at 80℃; for 6h; Suzuki-Miyaura Coupling;	99%
With palladium diacetate; sodium carbonate In ethanol; water at 80℃; for 4h; Suzuki-Miyaura Coupling;	98%

5-bromopyrimidine (4595-59-9) + N,N-diisopropylprop-2-yn-1-amine (6323-87-1) → N,N-diisopropyl-3-pyrimidin-5-ylprop-2-ynylamine

Conditions	Yield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In acetonitrile at 60℃; for 6h; Sonogashira coupling reaction;	99%

pyrrolidine (123-75-1) + 5-bromopyrimidine (4595-59-9) → 5-(pyrrolidin-1-yl)pyrimidine

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; nickel(II) bromide dimethoxyethane; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate In dimethyl sulfoxide at 80℃; for 0.166667h; Flow reactor; Sealed tube; Schlenk technique; Inert atmosphere; Irradiation;	99%
Stage #1: pyrrolidine; 5-bromopyrimidine With nickel(II) chloride hexahydrate; cadmium(II) sulphide In N,N-dimethyl acetamide for 0.00277778h; Schlenk technique; Sonication; Stage #2: In N,N-dimethyl acetamide at 20℃; for 24h; Schlenk technique; Irradiation;	98%
With dibenzylphosphoramidous acid 1,1'-binaphthyl-2,2'-diyl ester; caesium carbonate; copper(I) bromide In N,N-dimethyl-formamide at 90℃; for 36h;	83%
With sodium t-butanolate; XPhos; tris(dibenzylideneacetone)dipalladium (0) In toluene at 100℃; for 15h;	48%

5-bromopyrimidine (4595-59-9) + 4-methylphenylboronic acid (5720-05-8) → 5-(4-methyl phenyl)pyrimidine (74963-04-5)

Conditions	Yield
With potassium phosphate tribasic heptahydrate; palladium diacetate In ethylene glycol at 80℃; for 0.116667h; Suzuki coupling;	99%
With potassium phosphate tribasic heptahydrate; palladium diacetate In isopropyl alcohol at 80℃; for 0.5h; Suzuki coupling;	97%
With potassium phosphate tribasic heptahydrate; palladium dichloride In ethanol; water at 80℃; for 1h; Suzuki-Miyaura reaction;	93%

5-bromopyrimidine (4595-59-9) + (1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (113451-59-5) → tert-butyl (1S,4S)-5-(5-pyrimidinyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Conditions	Yield
	99%
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 80 - 85℃; for 5h;	91%
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 80 - 85℃; for 5h;	91%

5-bromopyrimidine (4595-59-9) + 4-formylphenylboronic acid, (87199-17-5) → 4-(pyrimidin-5-yl)benzaldehyde (198084-12-7)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 90℃; for 18h; Suzuki Coupling;	99%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate monohydrate In 1,2-dimethoxyethane; water at 90℃; Suzuki Coupling; Inert atmosphere;

5-bromopyrimidine (4595-59-9) + 4-n-methylphenylacetylene (766-97-2) → 5-((4-methylphenyl)ethynyl)pyrimidine (1058710-38-5)

Conditions	Yield
With copper(l) iodide; potassium tetrachloropalladate(II); N,N,N,N,-tetramethylethylenediamine; di‐tert‐butyl‐(1‐phenylindol‐2‐yl)phosphane at 80℃; for 20h; Sonogashira coupling; Inert atmosphere;	99%
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl acetamide at 50℃; for 48h; Sonogashira Cross-Coupling; Inert atmosphere;	82%
With 1,4-diaza-bicyclo[2.2.2]octane In water at 100℃; for 48h; Catalytic behavior; Sonogashira Cross-Coupling;	77%
With copper(l) iodide; Pd(t-Bu3P)2; diethylamine In N,N-dimethyl-formamide at 70℃; for 0.166667h; Sonogashira coupling; Microwave irradiation;
With potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 4h; Sonogashira Cross-Coupling;	97 %Chromat.

5-bromopyrimidine (4595-59-9) + Thien-3-ylboronic acid (6165-69-1) → 3-(pyrimidin-5-yl)thiophene (58759-02-7)

Conditions	Yield
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); triethylamine In water at 20℃; for 6h; Suzuki-Miyaura coupling; Inert atmosphere;	99%
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; Ni(4-CF3stb)3 In 1,4-dioxane at 80℃; for 8h; Inert atmosphere;	99%
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; Ni(COD)(DQ) In 1,4-dioxane at 80℃; for 8h; Suzuki-Miyaura Coupling; Sealed tube; Inert atmosphere;	98%

5-bromopyrimidine (4595-59-9) + 4-methoxyphenylacetylen (768-60-5) → 5-((4-methoxyphenyl)ethynyl)pyrimidine (1252609-00-9)

Conditions	Yield
With copper(l) iodide; potassium tetrachloropalladate(II); N,N,N,N,-tetramethylethylenediamine; di‐tert‐butyl‐(1‐phenylindol‐2‐yl)phosphane at 80℃; for 20h; Sonogashira coupling; Inert atmosphere;	99%

5-bromopyrimidine (4595-59-9) + furan-3-boronic acid (55552-70-0) → 5-(3-furan-3-yl)pyrimidine

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; Ni(COD)(DQ) In 1,4-dioxane at 80℃; for 8h; Suzuki-Miyaura Coupling; Sealed tube; Inert atmosphere;	99%
With potassium phosphate; NiCl2(PCy3)2 In 2-methyltetrahydrofuran at 100℃; for 12h; Solvent; Temperature; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube;	97%
With potassium phosphate; C28H31ClN2Ni; triphenylphosphine In toluene; tert-butyl alcohol at 90℃; for 1h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube;	94%

5-bromopyrimidine (4595-59-9) + (4-chlorophenyl)zinc(II) chloride (89523-62-6) → 5-(4-chlorobenzyl)pyrimidine (1401217-87-5)

Conditions	Yield
With lithium chloride; bis(triphenylphosphine)nickel(II) chloride In tetrahydrofuran at 0℃; for 5h; Product distribution / selectivity;	99%

5-bromopyrimidine (4595-59-9) + 2-benzofuranylboronic acid mida ester (1104637-65-1) → 5-(benzofuran-2-yl)pyrimidine

Conditions	Yield
With dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium; TPGS-750-M; triethylamine In water at 20℃; Inert atmosphere;	99%
With dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium; triethylamine In water at 20℃; for 6h; Suzuki Coupling;	90%

5-bromopyrimidine (4595-59-9) + 4-methyl-2,6-dioxo-8-phenylhexahydro-[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium-8-uide (109674-45-5) → 5-phenylpyrimidine (34771-45-4)

Conditions	Yield
With potassium phosphate; [Pd(η(5)-C5H5)Fe(η(5)-C5H3-C(CH3)=N-C6H4-4-CH3)Cl(P(C6H5)3)] In ethanol; water at 90℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Green chemistry;	99%

5-bromopyrimidine (4595-59-9) + potassium hexacyanoferrate(II) trihydrate → pyrimidine-5-carbonitrile (40805-79-6)

Conditions	Yield
With Palladium Nanoparticles with two shape-persistent covalent cages CC1' In N,N-dimethyl-formamide at 140℃; for 15h; Reagent/catalyst; Inert atmosphere;	99%

5-bromopyrimidine (4595-59-9) + S-(4-methoxyphenyl)-S-methylsulfoximine (77970-95-7) → (4-methoxyphenyl)(methyl)(pyrimidin-5-ylimino)-λ6-sulfanone

Conditions	Yield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; nickel(II)-4,4'-di(tert-butyl-2,2'-bipyridine) bromide; N,N,N',N'-tetramethylguanidine In N,N-dimethyl acetamide at 25℃; for 17h; Sealed tube; Inert atmosphere; Irradiation;	99%

5-bromopyrimidine (4595-59-9) + (1-methyl-1H-indol-5-yl)boronic acid → 1-methyl-5-(pyrimidin-5-yl)-1H-indole

Conditions	Yield
With potassium phosphate monohydrate; C50H60F3NO6PPdS In water at 55℃; for 5h; Suzuki-Miyaura Coupling;	99%

5-bromopyrimidine (4595-59-9) + 2-(4-fluorophenyl)-7-methylimidazo[1,2-a]pyridine → 2-(4-fluorophenyl)-7-methyl-3-(pyrimidin-5-yl)imidazo[1,2-a]pyridine

Conditions	Yield
With [Pd(IPr*IMe)An(3-Cl-pyridinyl)Cl2]; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;	99%

5-bromopyrimidine (4595-59-9) + 2-Methylphenylboronic acid (16419-60-6) → 5-(2-methylphenyl)pyrimidine

Conditions	Yield
With sodium carbonate; palladium 10% on activated carbon for 24h; Heating / reflux;	98.7%
With Tedicyp; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In xylene at 130℃; for 20h; Suzuki cross-coupling reaction;	80%

Upstream product

• 183438-24-6 5-bromo-2-iodopyrimidine 
• 136902-53-9 5-bromo-2-(5-bromothiophen-2-yl)pyridine 
• 36082-50-5 2,4-dichloro-5-bromopyrimidine 
• 7726-95-6 bromine 
• 30680-61-6 pyrimidine hydrochloride 
• 766-38-1 mucobromic acid 
• 77287-34-4 formamide 
• 37131-87-6 5-bromo-2-pyrimidinecarboxylic acid 

Downstream Products

• 216309-28-3 5-[(trimethylsilyl)ethynyl]pyrimidine 
• 141075-04-9 5-(phenylsulfanyl)pyrimidine 
• 430439-81-9 5-phenoxypyrimidine 
• 14257-02-4 5-metiltiopirimidina 
• 2036-41-1 5-methylpyrimidine 
• 672964-82-8 {(R)-1-[((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-4-pyrimidin-5-yl-butyl}-carbamic acid benzyl ester 
• 157911-66-5 pyrimidin-5-yl-(4-trifluoromethyl-phenyl)-amine 
• 64858-29-3 5-(pyridine-2-yl)pyrimidine 
• 865761-52-0 N-(5-pyrimidinyl)-N-methylphenylamine 
• 148854-13-1 5-(trimethylsilyl)pyrimidine 
• 70300-61-7 1-(4-chloro-phenoxy)-3,3-dimethyl-2-pyrimidin-5-yl-butan-2-ol 
• 1029095-90-6 (Z)-3-(3,4-dimethoxyphenyl)-3-(pyrimidin-5-yl)acrylonitrile 
• 1029095-92-8 (E)-3-(3,4-dimethoxyphenyl)-3-(pyrimidin-5-yl)acrylonitrile 
• 333792-86-2 5-(4-methyl-3-nitrophenyl)-pyrimidine 

Relevant articles and documents

Consecutive SNH and Suzuki-Miyaura cross-coupling reactions-an efficient synthetic strategy to pyrimidines bearing pyrrole and indole fragments

The combination of the Suzuki-Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen reactions is a versatile tool for the syntheses of 4-(1R-pyrrol-2-yl)-and 4-(1R-indol-3-yl)-5-(hetero)aryl-substituted pyrimidines from commercially available 5-bromopyrimidine. The S NH [AE, (addition-elimination)] and SN H [AO, (addition-oxidation)] reactions of 5-bromopyrimidine with pyrroles and indoles were studied by gas chromatography-mass spectrometry. The structures of the intermediate σH adducts as well as the pyrrole-(hetero)arylpyrimidine and indole-(hetero)arylpyrimidine dyads were established for the first time by X-ray crystal structure analysis.

Pyrimidine compounds

Pyrimidine derivatives of formula (I) wherein: Q1 and Q2 are independently selected from aryl or carbon linked heteroaryl optionally substituted as defined within; and one of Q1 and Q2 or both Q1 and Q2 is substituted on a ring carbon by one group selected from sulphamoyl, N—(C1-4alkyl)sulphamoyl (optionally substituted by halo or hydroxy), N,N-di-(C1-4alkyl)sulphamoyl (optionally substituted by halo or hydroxy), C1-4alkylsulphonyl (optionally substituted by halo or hydroxy) or a substituent of the formula (Ia) or (Ia′): wherein Q1, Q2, G, R1, Y, Z, Q3, n and m are as defined within; and pharmaceutically acceptable salts and in vivo hydrolysable esters thereof are described. Processes for their manufacture, pharmaceutical compositions and their use as cyclin-dependent serine/threonine kinase (CDK) inhibitors are also described.

Process for preparing 5-halopyrimidines

The reaction of formamide at high temperature with a 4-halo-5-hydroxy-2(5H)-furanone provides high yields of 5-chloro or 5-bromopyrimidines.