7226-23-5

Basic information

• Product Name: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone
• Synonyms: 1,3-dimethyl-perhydro-2-pyrimidinone;1,3-dimethyl-tetrahydro-pyrimidin-2-one;n,n’-dimethyltrimethyleneurea;tetrahydro-1,3-dimethyl-2(1h)pyrimidine;tetrahydro-1,3-dimethyl-2(1h)-pyrimidinon;1,3-Dimethyl-2-oxohexahydropyrimidine;1,3-Dimethyl-3,4,5,6-tetrahydropyrimidin-2(1H)-one;tetrahydro-1,3-dimethyl-1H-pyrimidin-2-one
• CAS NO: 7226-23-5
• Molecular Formula: C₆H₁₂N₂O
• Molecular Weight: 128.17228
• EINECS: 230-625-6
• Product Categories: Aliskiren
• Mol File: 7226-23-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: -20 °C
• Boiling Point: 146 °C44 mm Hg(lit.)
• Flash Point: 121 °C
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.06 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.082mmHg at 25°C
• Refractive Index: n20/D 1.488(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: -0.65±0.20(Predicted)
• Explosive Limit: 1.6-9.3%(V)
• Water Solubility: soluble
• Sensitive: Hygroscopic
• Stability: Hygroscopic
• BRN: 110562
• CAS DataBase Reference: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone(7226-23-5)
• EPA Substance Registry System: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone(7226-23-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-43-62-41
• Safety Statements: 23-26-36/37/39-45
• WGK Germany: 2
• RTECS: UW7582500
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 7226-23-5(Hazardous Substances Data)

Usage

Chemical Properties

1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone is clear colorless to slightly yellowish liquid

Uses

Different sources of media describe the Uses of 7226-23-5 differently. You can refer to the following data:
1. 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone is a versatile organic solvent in and less toxic than HMPA. It is mainly applied in the synthesis of pharmaceuticals and agrochemicals. DMPU is also used in the electronics industry.
2. 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone is a versatile solvent used in the N-alkylation of chiral and O-alkylation of aldoses. It is involved in the preparation of poly(aryl ethers). It is a cyclic urea and used as a polar aprotic organic solvent. Further, it reacts with trifluoro-methanesulfonic acid anhydride to prepare 2,2'-oxy-bis(1,3-dimethyl-tetrahydropyrimidinium) bis(trifluoromethanesulfonate).
3. Versatile solvent employed in N-alkylation of chiral, primary amines, O-alkylation of aldoses, and in the synthesis of poly(aryl ethers).

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C5H10.CH4N2O/c1-4-5(2)3;2-1(3)4/h4H,1-3H3;(H4,2,3,4)

Synthetic route

carbon monoxide (201230-82-2) + 1,3-bis(methylamino)propane (111-33-1) → 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5)

Conditions	Yield
Stage #1: carbon monoxide; 1,3-bis(methylamino)propane With selenium at 20℃; under 750.075 Torr; for 2h; neat (no solvent); Stage #2: With oxygen at 20℃; under 750.075 Torr; for 1h; neat (no solvent);	94%
With iodine; potassium carbonate; tungsten hexacarbonyl In dichloromethane at 20℃; under 76005.1 Torr;	52%

β-(4-hydroxyphenyl)ethyl iodoacetamide (53527-07-4) + 3-(((3-acetamido-4-methoxy-2-methyl-4-oxobutan-2-yl)disulfanecarbonyl)(methyl)amino)-N-methylpropan-1-aminium trifluoroacetate → 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + β-(4-hydroxyphenyl)ethyl-2-aminoacetamide (55710-99-1) + methyl 2-acetamido-3-((2-((4-hydroxyphenethyl)amino)-2-oxoethyl)disulfaneyl)-3-methylbutanoate + C18H26N2O5S

Conditions	Yield
With diethylenetriaminopentaacetic acid In aq. buffer at 37℃; for 7h; pH=7.4; Kinetics; Solvent; pH-value;	A n/a B n/a C 90% D n/a

3,4,5,6-tetrahydropyrimidine-2-thione (2055-46-1) + methyl iodide (74-88-4) → 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride for 5h; Heating;	81%
With 18-crown-6 ether; N-benzyl-N,N,N-triethylammonium chloride for 2h; Heating;	81%

3,4,5,6-tetrahydropyrimidin-2(1H)-one (1852-17-1) + dimethyl sulfate (77-78-1) → 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In 1,4-dioxane at 60℃; for 5h;	78.8%

2,2'-oxy-bis(1,3-dimethyl-tetrahydropyrimidinium) bis(trifluoromethanesulfonate) + malononitrile (109-77-3) → 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + (1,3-dimethyl-tetrahydro-pyrimidin-2-ylidene)-malononitrile (55727-22-5)

Conditions	Yield
With dimethylaminomethyl-polystyrene In acetonitrile at 81℃; for 8.5h;	A n/a B 78%

carbon dioxide (124-38-9) + 1,3-Dichloropropane (142-28-9) + methylamine (74-89-5) → 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + 3-methyl-1,3-oxazinan-2-one (96690-06-1)

Conditions	Yield
In water at 120℃; under 3750.38 Torr; for 2h;	A 64% B 15%

N-(tert-butyl)oxycarbonyl-N,N’-trimethyl-1,3-diaminopropane (123183-72-2) → 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 5 h / 0 - 20 °C 2: dichloromethane / 1 h / 20 °C / Inert atmosphere 3: 37 °C / pH 5.5 View Scheme
Multi-step reaction with 3 steps 1: triethylamine / N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere 2: dichloromethane / 1 h / 20 °C / Inert atmosphere 3: 37 °C / pH 5.5 View Scheme

1,3-bis(methylamino)propane (111-33-1) → 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrahydrofuran / 22 h / 0 - 20 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 5 h / 0 - 20 °C 3: dichloromethane / 1 h / 20 °C / Inert atmosphere 4: 37 °C / pH 5.5 View Scheme
Multi-step reaction with 4 steps 1: tetrahydrofuran / 22 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere 3: dichloromethane / 1 h / 20 °C / Inert atmosphere 4: 37 °C / pH 5.5 View Scheme

C28H32N4O6*C2HF3O2 → 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5)

Conditions	Yield
at 37℃; pH=5.5;

C26H28N4O5*C2HF3O2 → 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5)

Conditions	Yield
at 37℃; pH=5.5;

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + bis(pinacol)diborane (73183-34-3) → 1-methyl-3-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)tetrahydropyrimidin-2(1H)-one (1391930-67-8)

Conditions	Yield
With C25H36O2P2Ru In neat (no solvent) at 120℃; for 24h; Catalytic behavior; Green chemistry;	98%
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 8-(diisopropylsilyl)quinoline In 1,4-dioxane at 120℃; for 20h; Inert atmosphere; Sealed tube;	96%
With methoxy(cyclooctadiene)rhodium(I) dimer In hexane at 40℃; for 1h; Inert atmosphere; Sealed tube;	75%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + samarium diiodide bis(tetrahydrofuran) (94138-28-0) → [Sm(dimethylpropyleneurea)6]I2

Conditions	Yield
In tetrahydrofuran 6-fold excess of ligand added to soln. of Sm complex in THF at room temp. under Ar; left to stand for 2 h; evapd., washed with toluene; elem. anal.; X-ray detn.;	97%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + bis(pinacol)diborane (73183-34-3) → 1-methyl-3-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)tetrahydropyrimidin-2(1H)-one (1391930-67-8) + C3H6N(CH3)CONCH(BO2C2(CH3)4)2

Conditions	Yield
With methoxy(cyclooctadiene)rhodium(I) dimer In hexane at 25℃; for 1h; Inert atmosphere; regioselective reaction;	A 97% B 7%
With catalyst:[Rh(OCH3)(C8H12)]2 and silicaphosphine In hexane diboron, amide, catalyst:(Rh(OCH3)(C8H12))2, silica-supported triarylphosphine, hexane, 25°C, 1 h or 70°C 3 h;	A 85% B 2%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + methylamine hydroiodide (14965-49-2) + lead(II) iodide → CH6N(1+)*Pb(2+)*3I(1-)*2C6H12N2O

Conditions	Yield
at 80℃; for 0.5h;	96%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + Pentafluoroethyl iodide (354-64-3) + diethylzinc (557-20-0) → Zn(C2F5)2(1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone)2

Conditions	Yield
In hexane; toluene at -35 - -5℃; for 24h; Inert atmosphere;	95%
In hexane at -60 - 0℃; for 48h; Inert atmosphere;	86%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + 1,1,1,2,2,3,3-heptafluoro-3-iodo-propane (754-34-7) + diethylzinc (557-20-0) → Zn(nC3F7)2(1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone)2

Conditions	Yield
In hexane at -60 - -20℃; for 48h; Inert atmosphere;	95%
In hexane; toluene at -35 - -5℃; for 24h; Inert atmosphere;	93%
In hexane; toluene at -41 - -5℃; for 12h; Inert atmosphere;	92%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + Pentafluoroethyl iodide (354-64-3) + diethylzinc (557-20-0) → C4F10Zn*2C6H12N2O

Conditions	Yield
In hexane; toluene at -35 - -5℃; for 24h; Inert atmosphere;	95%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + iododifluoromethane (1493-03-4) + diethylzinc (557-20-0) → (1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone)2Zn(CF2H)2

Conditions	Yield
In hexane; pentane at -20 - 20℃; Inert atmosphere; Glovebox;	94%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + 1,1,1,2,2,3,3-heptafluoro-3-iodo-propane (754-34-7) + diethylzinc (557-20-0) → C6F14Zn*2C6H12N2O

Conditions	Yield
In hexane; toluene at -35 - -5℃; for 24h; Inert atmosphere;	93%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + triphenyltin dimesylamide (172747-89-6) → triphenyltin(IV)-dimesylamide-N,N'-dimethylpropyleneurea (1/1)

Conditions	Yield
In acetonitrile N2 atm.; equimolar ratio, stirring (20°C), refluxing (2 h); evapn., addn. of Et2O, digestion, filtn., washing (Et2O), drying (vac.);elem. anal.;	92%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + dodecafluoro-1,6-diiodohexane (375-80-4) + diethylzinc (557-20-0) → [(1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone)2Zn((CF2)6)2Zn(1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone)2]

Conditions	Yield
Stage #1: dodecafluoro-1,6-diiodohexane; diethylzinc In hexane; pentane at -78 - 20℃; Inert atmosphere; Glovebox; Stage #2: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In hexane; pentane at 20℃; Inert atmosphere; Glovebox;	92%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + iododifluoromethane (1493-03-4) + diethylzinc (557-20-0) → [bis(difluoromethyl)zinc(dmpu)2]

Conditions	Yield
In hexane Inert atmosphere;	92%
In hexane; pentane at -20 - 20℃; for 2h;	89%
In hexane; pentane at -20 - 20℃; for 2h;	89%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + 2-amino-benzthiazole (136-95-8) → Benzothiazol-2-ylamine; compound with 1,3-dimethyl-tetrahydro-pyrimidin-2-one (144467-83-4)

Conditions	Yield
In toluene at 0℃; for 24h;	91%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + {(η5-C5Me5)2YCl}2 (94348-89-7) → (C5(CH3)5)2YCl((CH2)3(NCH3)2CO) (431887-85-3)

Conditions	Yield
In benzene (N2); addn. of a soln. of ligand in benzene to a slurry of yttrium complex in benzene, stirring for 1 h; evapn.; elem. anal.;	90%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + iodotrifluoromethane (2314-97-8) + diethylzinc (557-20-0) → (1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone)2Zn(CF3)2

Conditions	Yield
In hexane at -60 - -20℃; for 48h; Inert atmosphere;	90%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + iodotrifluoromethane (2314-97-8) + diethylzinc (557-20-0) → (CF3)2Zn(DMPU)2

Conditions	Yield
In hexane at -60 - -20℃; for 72h; Inert atmosphere;	90%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + iodotrifluoromethane (2314-97-8) + diethylzinc (557-20-0) → C6H12N2O*C2F6Zn

Conditions	Yield
In hexane at -60 - -20℃; for 72h; Inert atmosphere;	90%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + 9H-carbazole (86-74-8) + 2,2'-diiodobiphenyl (2236-52-4) → 9-(4'-iodine-[1,1'-biphenyl]-4-yl)-9H-carbazole (207447-27-6)

Conditions	Yield
With potassium carbonate; 18-crown-6 ether; copper(I) iodide In hexane; water; toluene	89%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) + diethylzinc (557-20-0) → C8F18Zn*2C6H12N2O

Conditions	Yield
In toluene at -35 - -5℃; for 24h; Inert atmosphere;	89%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) + diethylzinc (557-20-0) → Zn(C4F9)2(DMPU)2

Conditions	Yield
In hexane; toluene at -35 - -5℃; for 24h; Inert atmosphere;	89%
In hexane at -35 - -5℃; for 24h; Inert atmosphere;	89%
In hexane; toluene at -41 - -5℃; for 12h; Inert atmosphere;	88%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + n-perfluorohexyl iodide (355-43-1) + diethylzinc (557-20-0) → Zn(nC6F13)2(1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone)2

Conditions	Yield
In hexane at -60 - 0℃; for 48h; Inert atmosphere;	88%
In hexane; toluene at -35 - -5℃; for 24h; Inert atmosphere;	88%
In hexane; toluene at -41 - -5℃; for 12h; Inert atmosphere;	87%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + n-perfluorohexyl iodide (355-43-1) + diethylzinc (557-20-0) → C12F26Zn*2C6H12N2O

Conditions	Yield
In hexane; toluene at -35 - -5℃; for 24h; Inert atmosphere;	88%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + stavudin (3056-17-5) → 2',3'-didehydro-3'-deoxythymidine N,N-dimethyl propylene urea solvate (938050-90-9)

Conditions	Yield
In acetone at 56℃; for 0.25 - 0.5h; Product distribution / selectivity; Heating / reflux;	87.5%
In acetone at 6 - 56℃; for 0.25h; Product distribution / selectivity;	87.5%
In isopropyl alcohol at 70 - 75℃; for 0.25h; Product distribution / selectivity;	86.7%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + triphenyltin dimesylamide (172747-89-6) → triphenyltin(IV)-dimesylamide-N,N'-dimethylpropyleneurea (1/2)

Conditions	Yield
In acetonitrile N2 atm.; 2 equiv. of ligand, stirring (20°C), refluxing (2 h); evapn., addn. of Et2O, digestion, filtn., washing (Et2O), drying (vac.);elem. anal.;	87%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + 3-(3-bromophenyl)-1,2,4-triazolo[3,4-a]isoquinoline (1356922-21-8) + 9H-carbazole (86-74-8) → 3-[3-(9H-carbazol-9-yl)phenyl]-1,2,4-triazolo[3,4-a]isoquinoline (1356922-22-9)

Conditions	Yield
With sodium bicarbonate; potassium carbonate; copper(I) iodide; 18-crown-6 ether In chloroform	86%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + samarium(III) trifluoromethanesulfonate → [Sm(1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone)6](O3SCF3)3

Conditions	Yield
In tetrahydrofuran Ar-atmosphere; addn. of 6 equiv. ligand to metal salt, standing for 1 h; solvent removal (reduced pressure);	85%

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + formamidinium iodide + lead(II) iodide → CH5N2(1+)*Pb(2+)*3I(1-)*2C6H12N2O

Conditions	Yield
at 90℃; for 0.5h;	85%

5-methyl-1,2,3,4-tetrazole (4076-36-2) + 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + zinc(II) nitrate hexahydrate + ethanol (64-17-5) → Zn(5-methyltetrazole(-H))2·0.5(tetrahydro-1,3-dimethyl-2(1H) pyrimidine)·0.5(ethanol)

Conditions	Yield
at 120℃; for 72h; Sealed tube;	84%

Upstream product

• 124-38-9 carbon dioxide 
• 142-28-9 1,3-Dichloropropane 
• 74-89-5 methylamine 
• 111-33-1 1,3-bis(methylamino)propane 
• 123183-72-2 N-(tert-butyl)oxycarbonyl-N,N’-trimethyl-1,3-diaminopropane 
• 7218-04-4 N-Acetylcysteine 
• 53527-07-4 β-(4-hydroxyphenyl)ethyl iodoacetamide 
• 107-06-2 1,2-dichloro-ethane 
• 201230-82-2 carbon monoxide 
• 75-44-5 phosgene 
• 108-88-3 toluene 
• 109-77-3 malononitrile 
• 105-56-6 ethyl 2-cyanoacetate 
• 2055-46-1 3,4,5,6-tetrahydropyrimidine-2-thione 

Downstream Products

• 170497-69-5 1-N,N-dimethylcarbamoyl-6-(4-fluorophenyl)-3-{4-[(1H-2-methylimidazo[4.5-c]pyrid-1-yl)methyl]benzoyl}indole 
• 1467101-19-4 (Z)-1,3-dimethyl-4-styryltetrahydropyrimidin-2(1H)-one 
• 1467101-29-6 (E)-1,3-dimethyl-4-styryltetrahydropyrimidin-2(1H)-one 
• 300355-19-5 3-cyclopentyl-2-(4-methanesulfonyl-phenyl)propionic acid methyl ester 
• 372509-76-7 3-cyclopentyl-2-(4-morpholin-4-yl-phenyl)-propionic acid methyl ester 
• 391935-67-4 1-[[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenyl]sulfonyl]-2,4-imidazolidinedione 

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