5807-14-7

Basic information

• Product Name: 1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO[1,2-A]PYRIMIDINE
• Synonyms: LABOTEST-BB LT00847641;1,5,7-TRIAZABICYCLO[4.4.0]DEC-5-ENE;1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO[1,2-A]PYRIMIDINE;1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO[1,2-A]PYRIMIDINE, POLYMER-BOUND;TBD;2H-Pyrimido[1,2-a]pyrimidine, 1,3,4,6,7,8-hexahydro-;1,5,7-Triazabicylo[4.4.0]dec-5-ene;Silicagel, functionalized, 1,5,7-Triazabicyclo[4,4,0]dec-5-ene, 1.4
• CAS NO: 5807-14-7
• Molecular Formula: C₇H₁₃N₃
• Molecular Weight: 139.2
• EINECS: 227-367-1
• Product Categories: Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;N-Containing;Others
• Mol File: 5807-14-7.mol
• Article Data: 16

Chemical Properties

• Melting Point: 125-130 °C(lit.)
• Boiling Point: 222.3 °C at 760 mmHg
• Flash Point: 88.3 °C
• Appearance: /
• Density: 1.28 g/cm³
• Vapor Pressure: 0.102mmHg at 25°C
• Refractive Index: 1.656
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: toluene: soluble1 g/15 mL
• PKA: 14.47±0.20(Predicted)
• BRN: 3242
• CAS DataBase Reference: 1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO[1,2-A]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO[1,2-A]PYRIMIDINE(5807-14-7)
• EPA Substance Registry System: 1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO[1,2-A]PYRIMIDINE(5807-14-7)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-27
• RIDADR: UN 1759 8/PG 2
• WGK Germany: 3
• F: 9-21-34
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 5807-14-7(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow crystalline

Uses

1,5,7-Triazabicyclo[4.4.0]dec-5-ene may be used as organocatalyst for aminolysis of esters. It may be used as catalyst for direct addition of P(O)-H bonds (dialkyl phosphites and diphenyl phosphonite) across various activated alkenes. Polymer supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene (PTBD) was used as a base and a reagent scavenger for the synthesis of aryl ethers from phenols and alkyl or aryl halides.

General Description

1,5,7-Triazabicyclo[4.4.0]dec-5-ene, a bicyclic guanidine base, has been found to be an excellent catalyst for Michael and Michael-type reactions. It forms 1:1 complex with lasalocid acid and crystal structure of the complex has been studied by X-ray diffraction, FT-IR spectroscopy and 1H NMR.

Purification Methods

1,5,7-Triazabicyclo[4.4.0]dec-5-ene crystallises from Et2O but readily forms white crystals of the carbonate. It is a strong base (see pK, i.e. about 100 times more basic than tetramethylguanidine). The picrate has m 220.5-222o (from EtOH). It forms the 5-nitro derivative m 14.5-160o that gives a 5-nitro nitrate salt m 100-101o (from EtOH/Et2O) and a 5-nitro picrate m 144-145o (from H2O) [McKay & Kreling Can J Chem 35 1438 1957, Schwesinger Chimia 39 369 1985, Hilpert et al. J Chem Soc, Chem Commun 1401 1983, Kamfen & Eschenmoser Helv Chim Acta 72 185 1989]. [Beilstein 26 III/IV 60.]

InChI:InChI=1/C7H13N3/c1-3-8-7-9-4-2-6-10(7)5-1/h1-6H2,(H,8,9)

Synthetic route

bis(3-aminopropyl)amine (56-18-8) + guanidine hydrochloride (50-01-1) → 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7)

Conditions	Yield
Stage #1: bis(3-aminopropyl)amine; guanidine hydrochloride With hydrogenchloride at 155℃; Stage #2: With sodium methylate In methanol	93%
With anion exchange resin (D201) In water; 1,3,5-trimethyl-benzene at 120℃; for 9h; Temperature; Autoclave; Inert atmosphere;	55%

bis(3-aminopropyl)amine (56-18-8) + isooctyltriethoxysilane + carbonic acid dimethyl ester (616-38-6) → 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7)

Conditions	Yield
Stage #1: bis(3-aminopropyl)amine; carbonic acid dimethyl ester at 60 - 250℃; for 4h; Stage #2: isooctyltriethoxysilane at 250℃; for 9h; Temperature; Reagent/catalyst;	87%

bis(3-aminopropyl)amine (56-18-8) + di-p-tolylcarbodiimide (726-42-1) → 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7)

Conditions	Yield
With [ς:η1:η5-(OCH2)(Me2NCH2)C2B9H9]Ti-(NMe2) In toluene at 115℃; for 240h;	76%
With 2-Butoxyethanol at 23 - 170℃; for 15h;

<3-chloro-propyl>-<1,4,5,6-tetrahydro-pyrimidin-2-yl>-amine hydrochloride → 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7)

Conditions	Yield
With potassium hydroxide

1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine tetraphenylborate (229311-99-3) → C24H21B + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7)

Conditions	Yield
In acetonitrile Quantum yield; Kinetics; Mechanism; Time; Concentration; UV-irradiation at 254 nm; Inert atmosphere;

1-(3-aminopropyl)tetrahydro-2(1H)-pyrimidinone (13173-07-4) → 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7)

Conditions	Yield
In Triethylene glycol dimethyl ether at 100 - 230℃; Product distribution / selectivity; Inert atmosphere;

7-acetyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene + N-butylamine (109-73-9) → N-butylacetamide (1119-49-9) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7)

Conditions	Yield
In (2)H8-toluene at 24.84℃; Kinetics; Inert atmosphere;

7-acetyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene + benzyl alcohol (100-51-6) → Benzyl acetate (140-11-4) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7)

Conditions	Yield
In (2)H8-toluene at 24.84℃; Kinetics; Inert atmosphere;

bis(3-aminopropyl)amine (56-18-8) + N-Cyanoguanidine (127099-85-8, 780722-26-1) → 2,4,6-triamino-s-triazine (108-78-1) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7)

Conditions	Yield
In 2-Butoxyethanol at 60 - 170℃; for 2h; Inert atmosphere;	A 47 %Spectr. B 34 %Spectr.

bis(3-aminopropyl)amine (56-18-8) + N-Cyanoguanidine (127099-85-8, 780722-26-1) → 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7)

Conditions	Yield
With carbon dioxide In 2-Butoxyethanol at 60 - 130℃; for 6h;	57 %Spectr.
With toluene-4-sulfonic acid at 220 - 230℃; for 6h; Inert atmosphere;

bis(3-aminopropyl)amine (56-18-8) + CYANAMID (420-04-2) → 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7)

Conditions	Yield
Stage #1: bis(3-aminopropyl)amine; CYANAMID With hydrogenchloride at 155℃; Stage #2: With sodium methylate In methanol

bis(3-aminopropyl)amine (56-18-8) + diisopropyl-carbodiimide (693-13-0) → 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7)

Conditions	Yield
With 2-Butoxyethanol; isopropylamine at 60 - 170℃; for 12h;

bis(3-aminopropyl)amine (56-18-8) + dicyclohexyl-carbodiimide (538-75-0) → 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7)

Conditions	Yield
With 2-Butoxyethanol at 60 - 170℃; for 18h; Reagent/catalyst; Temperature;

C15H10O4*C7H13N3 (1333123-53-7) → 2-methyl-9H-xanthen-9-one (6280-45-1) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7)

Conditions	Yield
In methanol UV-irradiation;

C7H13N3*C16H14O3 (1333123-47-9) → 3-ethylbenzophenone (66067-43-4) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7)

Conditions	Yield
In methanol UV-irradiation;

bis(3-aminopropyl)amine (56-18-8) → 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) + 1,3,4,6,7,8-hexahydro-1-methyl-2H-pyrimido[1,2-a]pyrimidine

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 16 h / 180 °C / 3750.38 - 45754.6 Torr / Autoclave 2: silica-doped aluminum oxide / methanol / 253 °C / 750.08 Torr / Inert atmosphere View Scheme

bis(3-aminopropyl)amine (56-18-8) + carbon dioxide (124-38-9) → 1-(3-aminopropyl)tetrahydro-2(1H)-pyrimidinone (13173-07-4) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) + 1-methyltetrahydropyrimidin-2(1H)-one (10166-54-8) + 1-ethyltetrahydropyrimidin-2(1 H)-one (66639-75-6)

Conditions	Yield
In methanol at 180℃; under 3750.38 - 45754.6 Torr; for 16h; Pressure; Solvent; Autoclave;

1-(3-aminopropyl)tetrahydro-2(1H)-pyrimidinone (13173-07-4) → 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) + 1,3,4,6,7,8-hexahydro-1-methyl-2H-pyrimido[1,2-a]pyrimidine

Conditions	Yield
With silica-doped aluminum oxide In methanol at 253℃; under 750.075 Torr; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;

2-(benzyloxy)propane-1,3-diyl bis(4-methylbenzenesulfonate) (19945-19-8) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → 2-(benzyloxy)octahydro-3a,6a,9a-triazaphenalene (160154-14-3)

Conditions	Yield
With potassium hydroxide; sodium tetrahydroborate; potassium bromide In toluene for 42.5h; Ambient temperature;	100%
Stage #1: 2-(benzyloxy)propane-1,3-diyl bis(4-methylbenzenesulfonate); 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine With potassium hydroxide In 1,4-dioxane for 48h; Heating; Stage #2: With sodium tetrahydroborate In 1,4-dioxane at 20℃; for 48h;

1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) + diisopropyl-carbodiimide (693-13-0) → (Z)-N,N′-diisopropyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine-1-carboximidamide

Conditions	Yield
at 20℃; for 48h; Inert atmosphere;	100%
With acid	43%

carbon dioxide (124-38-9) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → [TBDH][HCO3]

Conditions	Yield
With water In tetrahydrofuran at 20℃; under 760.051 Torr; for 0.5h;	100%

1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → tetrafluoroborate guanidinium salt

Conditions	Yield
With tetrafluoroboric acid In methanol; water at 0℃; for 0.5h;	100%

1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) + 1,3-Diamino-2-hydroxypropane (616-29-5) + Diethyl carbonate (105-58-8) → tetrahydro-5-hydroxy-2(1H)-pyrimidinone (1852-18-2)

Conditions	Yield
	100%

formic acid (64-18-6) + carbon dioxide (124-38-9) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → CH2O2*C7H13N3 (1356453-15-0)

Conditions	Yield
In diethyl ether at 30℃; under 750.075 Torr; for 1h; Inert atmosphere;	100%

1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) + p-Tolylisocyanate (622-58-2) → N-(p-tolyl)-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine-1-carboxamide

Conditions	Yield
In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	100%

1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) + 1-isothiocyanato-4-methylbenzene (622-59-3) → (Z)-N-p-tolyl-2,3,4,6,7,8-hexahydro-1H-pyrimido-[1,2-a]pyrimidin-9-ium-1-carbimidothioate

Conditions	Yield
In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	100%

1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) + p-trifluoromethyl-phenylisocyanate (1548-13-6) + benzene (71-43-2) → N-[4-(trifluoromethyl)phenyl]-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine-1-carboxamide

Conditions	Yield
In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	100%

2,2,2-trifluoroethanol (75-89-8) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → C7H14N3(1+)*C2H2F3O(1-)

Conditions	Yield
at 50℃; for 24h; Cooling with ice; Inert atmosphere;	100%

1,2-W2(i-Bu)2(NMe2)4 + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → W2(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine)4 (463931-34-2)

Conditions	Yield
In benzene (Ar); stirred for 3 d; evapd., dried, dissolved in C6H6, pptd. with hexane, filtered, washed (hexane), dried;	99%

1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine hydroiodide

Conditions	Yield
With hydrogen iodide In water at 0 - 20℃; for 2h;	99%
Multi-step reaction with 2 steps 1: ammonium chloride / methanol / 4 h / 20 °C / Inert atmosphere 2: sodium iodide / dichloromethane / 24 h / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: ammonium chloride / methanol / 1 h / 20 °C 2: sodium iodide / dichloromethane / 16 h / 20 °C View Scheme

W2Cl2(NMe2)4 + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → W2(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine)4Cl2 (280107-73-5, 874340-22-4)

Conditions	Yield
In melt byproducts: HNMe2; (N2 or Ar); W2Cl2(NMe2)4 placed together with ligand, finely ground, heated under Ar at 150°C for 15 h; evacuated on cooling, powdered finely, heated at 150°C under 1E-4Torr, recrystd. (CH2Cl2); elem. anal.;	98%

carbon dioxide (124-38-9) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → 2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidin-9-ium-9-carboxylate

Conditions	Yield
In tetrahydrofuran under 760.051 Torr;	98%
In tetrahydrofuran at 20℃; under 760.051 Torr; for 0.0833333h; Inert atmosphere;	98%
In tetrahydrofuran at 20℃; under 750.075 Torr; for 1h; Inert atmosphere; Schlenk technique;

(C5Me5)2Ce(η3-CH2CHCH2)(THF) (863223-65-8) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → (C5Me5)2Ce(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine)

Conditions	Yield
In toluene byproducts: C3H6, C4H8O; (Ar or N2); soln. of pyrimidine in toluene was added to soln. of cerium complex in toluene, stirred for 12 h; evapd. in vac., elem. anal.;	97%

(C5Me5)2Sm(η3-CH2CHCH2)(THF) (1085985-44-9) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → (C5Me5)2Sm(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine)

Conditions	Yield
In toluene byproducts: C3H6, C4H8O; (Ar or N2); soln. of pyrimidine in toluene was added to soln. of samarium complex in toluene, stirred for 12 h; evapd. in vac., elem. anal.;	97%

dimethylbis(η5-pentamethylcyclopentadienyl)uranium (67605-92-9) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → [UMe(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidinato)(pentamethylcyclopentadienyl)2] (1202368-33-9)

Conditions	Yield
In toluene byproducts: CH4; (N2); ligand was added with stirring to soln. of U complex in toluene; stirred for 12 h; evapd. (vac.); elem. anal.;	97%

[1-(N-pivaloylamino)ethyl]triphenylphosphonium tetrafluoroborate + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → 5-[1-(N-pivaloylamino)ethyl]-1,7-diaza-5-azoniabicyclo[4.4.0.]dec-5-ene tetrafluoroborate

Conditions	Yield
In acetonitrile at 20℃; for 0.166667h;	97%

[1-(N-benzyloxycarbonylamino)ethyl]triphenylphosphonium tetrafluoroborate + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → 5-[1-(N-benzyloxycarbonylamino)ethyl]-1,7-diaza-5-azoniabicyclo[4.4.0.]dec-5-ene tetrafluoroborate

Conditions	Yield
In acetonitrile at 20℃; for 0.166667h;	97%

1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) + acetic acid (64-19-7) → 1,5,7-triazabicyclo[4.4.0]dec-5-enium acetate

Conditions	Yield
In ethanol at 0 - 20℃; for 1h;	97%
In hexane at 0 - 20℃; for 24h; Inert atmosphere;

(C5Me5)2Y(η3-CH2CHCH2)(THF) (378753-31-2) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → (C5Me5)2Y(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine)

Conditions	Yield
In toluene byproducts: C3H6, C4H8O; (Ar or N2); soln. of pyrimidine in toluene was added to soln. of samarium complex in toluene, stirred for 12 h; evapd. in vac., elem. anal.;	96%

1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) + trimethylamine-gallane adduct (19528-13-3) → (H2Ga(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine(1-))2

Conditions	Yield
[(κ3-C6H3-1,3-[OPtBu2]2)Ir(H)2] In diethyl ether; toluene standard Schlenk techniques under an inert gas; Ga-compd. in Et2O cooledto 0°C, added to pyrimidine-compd. in toluene at -95°C wi th cannula, stirred for 1.5 h, solid Ir-compd. added at -52°C, stirred for 6 h, warmed to -18°C; kept at -18°C for two weeks, elem. anal.;	96%

2,5-dibromopyridine (624-28-2) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → 1-(5-bromopyridin-2-yl)-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (1537175-34-0)

Conditions	Yield
In neat (no solvent) at 90℃; for 3h; Sealed tube; Green chemistry;	96%
at 90℃; for 3h; Sealed tube;	96%

2-bromo-5-nitropyridine (4487-59-6) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → 1-(5-nitropyridin-2-yl)-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine

Conditions	Yield
Stage #1: 2-bromo-5-nitropyridine With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 60℃; Inert atmosphere; Stage #2: 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine With potassium tert-butylate In toluene at 120℃; for 3h; Inert atmosphere;	96%

carbon disulfide (75-15-0) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → 2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidin-9-ium 2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine-1-carbodithioate

Conditions	Yield
In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	96%

1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) + C27H30N2O5 → C27H30N2O5*2C7H13N3

Conditions	Yield
In methanol at 20℃; for 12h;	95.3%

Mo2Cl2(NMe2)4 + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → Mo2(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidinato)4Cl2 (603952-68-7, 645402-76-2)

Conditions	Yield
In melt byproducts: HNMe2; (N2 or Ar); Mo2Cl2(NMe2)4 placed together with ligand, finely ground, heated under Ar at 150°C for 12 h; evacuated on cooling, powdered finely, heated at 150°C under 1E-4Torr, recrystd. (CH2Cl2); elem. anal.;	95%

3-imidazolyl-3-(4-methoxyphenyl)propionic acid + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → C13H14N2O3*C7H13N3

Conditions	Yield
In methanol at 60℃; for 0.5h; Inert atmosphere;	95%
In methanol at 60℃; for 0.5h; Inert atmosphere;	95%

1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) + C25H26N2O5 → C25H26N2O5*2C7H13N3

Conditions	Yield
In methanol at 30℃; for 1h;	94.4%

1-chloro-2,3,4,5,6-pentafluorobenzene (344-07-0) + 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) → 12-chloro-11,13,14-trifluoro-1,5,9-triaza-tricyclo[7.6.1.010,15]hexadeca-10,12,14-trien-16-one

Conditions	Yield
With water In acetonitrile for 0.5h; Heating;	94%

Upstream product

• 229311-99-3 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine tetraphenylborate 
• 56-18-8 bis(3-aminopropyl)amine 
• 113-00-8 guanidine nitrate 
• 74569-04-3 3,4,6,7,8,9-Hexahydro-2H-pyrimido<1,2-a>pyrimidin-hydrobromid 
• 74569-03-2 Bis(3-aminopropyl)amin-trihydrobromid 
• 616-38-6 carbonic acid dimethyl ester 
• 13173-07-4 1-(3-aminopropyl)tetrahydro-2(1H)-pyrimidinone 
• 124-38-9 carbon dioxide 
• 1333123-47-9 C₇H₁₃N₃*C₁₆H₁₄O₃ 
• 1333123-53-7 C₁₅H₁₀O₄*C₇H₁₃N₃ 
• 538-75-0 dicyclohexyl-carbodiimide 
• 693-13-0 diisopropyl-carbodiimide 
• 50-01-1 guanidine hydrochloride 
• 420-04-2 CYANAMID 

Downstream Products

• 393826-57-8 [(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine)(cyano)2(triphenylphosphine)4dicopper(I)] 
• 686319-85-7 [CuBr(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine)(PPh₃)]2 
• 686319-83-5 CuCl(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine)(PPh₃) 
• 686319-87-9 [CuI(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine)(PPh₃)]2 
• 229311-99-3 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine tetraphenylborate 
• 1019265-59-8 1,5,7-triazabicyclo[4.4.0]dec-5-ene*4-nitrophenyl[bis(methylsulfonyl)]methane complex 

Relevant articles and documents

Super alkali material and preparation method thereof, and organic light-emitting diode

The invention discloses a super alkali material and a preparation method thereof, and an organic light-emitting diode. The super alkali material has a general structural formula as described in the specification. In the general structural formula, aromatic rings Ar1, Ar2, Ar3 and Ar4 are respectively and independently selected from substituted or unsubstituted aryl or heteroaryl groups; N is a nitrogen atom; E is the same or different, and each E is an sp2-hybridized carbon or nitrogen atom; and Cy1, Cy2, Cy3 and Cy4 are respectively and independently selected from substituted or unsubstituted heterocyclic rings. The electron injection performance of a device can be effectively improved by introducing a functional group with an alkaline acid dissociation constant (pKa), and a planar rigid structure is adopted, so the material is closely stacked to show high electron mobility, the glass-transition temperature (Tg) of the material is increased, and the stability of the device is improved. On the premise that HOMO and LUMO energy levels are maintained, injection energy barriers are reduced, turn-on voltage is reduced, and when the material serves as an electron transport material of the organic light-emitting diode, the material has the advantages of being high in carrier mobility, excellent in device performance, good in stability and the like.

PROCESS FOR PREPARING BICYCLIC GUANIDINES

Bicyclic guanidines are prepared by reacting dialkylenetriamines with dialkylcarbonates in the presence of a silane of the formula [in-line-formulae]Si(ORx)oRY(4?o) ??(IV)[/in-line-formulae] and/or their partial hydrolysates, with the proviso that contain minimally one unit IV which is a monovalent optionally substituted hydrocarbon radial with 3 to 10 carbon atoms.

METHOD FOR PREPARING A BICYCLIC GUANIDINE AND ITS DERIVATIVES

The present invention relates to a method of producing a bicyclic guanidine and its derivatives. In particular, the present invention relates to a method of producing triazabicyclodecene (TBD) and its derivatives, particularly alkyl derivatives, such as methyl triazabicyclodecene (MTBD), and MTBD-derived ionic liquids. The invention also relates to the use of said compounds in cellulose dissolution and subsequent processing.