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1,2-Dimethyl-1,4,5,6-tetrahydropyrimidine

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Name

1,2-Dimethyl-1,4,5,6-tetrahydropyrimidine

EINECS 224-262-2
CAS No. 4271-96-9 Density 0.98 g/cm3
PSA 15.60000 LogP 0.11380
Solubility Melting Point
Formula C6H12N2 Boiling Point 191.7 °C at 760 mmHg
Molecular Weight 112.17 Flash Point 69.8 °C
Transport Information 3267 Appearance Slight yellow to colorless
Safety 23-26-36/37/39 Risk Codes 22-34
Molecular Structure Molecular Structure of 4271-96-9 (1,2-Dimethyl-1,4,5,6-tetrahydropyrimidine) Hazard Symbols IrritantXi
Synonyms

1,2-Dimethyl-1,4,5,6-tetrahydropyrimidine;1,4,5,6-Tetrahydro-1,2-dimethylpyrimidine;2,3-Dimethyl-3,4,5,6-tetrahydropyrimidine;

 

1,2-Dimethyl-1,4,5,6-tetrahydropyrimidine Synthetic route

61327-70-6

1,2-dimethyl-hexahydro-pyrimidine

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

Conditions
ConditionsYield
With oxygen; gold In acetonitrile at 60℃; under 760.051 Torr; for 40h;97%
75-05-8

acetonitrile

6291-84-5

N-Methyl-1,3-propanediamine

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

Conditions
ConditionsYield
With thioacetamide at 90 - 110℃; for 6h; Temperature; Reagent/catalyst; Large scale;96%
Stage #1: acetonitrile; N-Methyl-1,3-propanediamine With zinc(II) chloride for 24h; Inert atmosphere; Reflux;
Stage #2: Inert atmosphere;
45%
56125-48-5

N-[3-(methylamino)propyl]acetamide

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

Conditions
ConditionsYield
With PPE at 80℃; for 2h; Temperature; Microwave irradiation;94.42%
2208-07-3

ethyl acetimidate hydrochloride

6291-84-5

N-Methyl-1,3-propanediamine

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

Conditions
ConditionsYield
at 125℃; for 15h; Yield given;
18871-66-4

N,N-dimethylacetamide dimethyl acetal

6291-84-5

N-Methyl-1,3-propanediamine

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

Conditions
ConditionsYield
In neat (no solvent) at 80℃; for 1h;5.33 g
4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine hydroiodide

Conditions
ConditionsYield
With hydrogen iodide In 1,4-dioxane; water at 0 - 20℃; for 12h;100%
1520-20-3

1-isothiocyanato-4-vinylbenzene

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

C15H19N3S

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 12h; Schlenk technique; Inert atmosphere;97%
1711-09-7

3-bromobenzoyl chloride

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

1228685-35-5

2-[1-(3-bromobenzoyl)-3-methyltetrahydropyrimidin-2(1H)-ylidene]-1,3-bis(3-bromophenyl)propane-1,3-dione

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Reflux;89%
4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

1711-07-5

3-fluorobenzoyl chloride

1228685-32-2

2-[1-(3-fluorobenzoyl)-3-methyltetrahydropyrimidin-2(1H)-ylidene]-1,3-bis(3-fluorophenyl)propane-1,3-dione

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Reflux;88%
403-43-0

4-fluorobenzoyl chloride

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

1228685-31-1

2-[1-(4-fluorobenzoyl)-3-methyltetrahydropyrimidin-2(1H)-ylidene]-1,3-bis(4-fluorophenyl)propane-1,3-dione

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Reflux;84%
100-07-2

4-methoxy-benzoyl chloride

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

1228685-29-7

2-[1-(4-methoxybenzoyl)-3-methyltetrahydropyrimidin-2(1H)-ylidene]-1,3-bis(4-methoxyphenyl)propane-1,3-dione

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Reflux;83%
98-88-4

benzoyl chloride

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

2-(1-benzoyl-3-methyltetrahydropyrimidin-2(1H)-ylidene)-1,3-diphenylpropane-1,3-dione

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Reflux;82%
With triethylamine In tetrahydrofuran Inert atmosphere;
874-60-2

4-methyl-benzoyl chloride

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

1228685-30-0

2-[1-methyl-3-(4-methylbenzoyl)tetrahydropyrimidin-2(1H)-ylidene]-1,3-bis(4-methylphenyl)propane-1,3-dione

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Reflux;82%
122-01-0

4-chloro-benzoyl chloride

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

1228685-28-6

2-[1-(4-chlorobenzoyl)-3-methyltetrahydropyrimidin-2(1H)-ylidene]-1,3-bis(4-chlorophenyl)propane-1,3-dione

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Reflux;80%
618-46-2

m-Chlorobenzoyl chloride

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

1228685-34-4

2-[1-(3-chlorobenzoyl)-3-methyltetrahydropyrimidin-2(1H)-ylidene]-1,3-bis(3-chlorophenyl)propane-1,3-dione

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Reflux;79%
1195-45-5

para-fluorophenyl isocyanate

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

1227407-98-8

N,7-bis(4-fluorophenyl)-1-methyl-6,8-dioxo-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,6-a]pyrimidine-9-carboxamide

Conditions
ConditionsYield
In acetonitrile at 20℃; Inert atmosphere; Reflux;76%
4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

1711-06-4

3-Methylbenzoyl chloride

1228685-36-6

2-[1-methyl-3-(3-methylbenzoyl)tetrahydropyrimidin-2(1H)-ylidene]-1,3-bis(3-methylphenyl)propane-1,3-dione

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Reflux;74%
622-58-2

p-Tolylisocyanate

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

1227407-96-6

1-methyl-6,8-dioxo-N,7-di-p-tolyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,6-a]pyrimidine-9-carboxamide

Conditions
ConditionsYield
In acetonitrile at 20℃; Inert atmosphere; Reflux;74%
103-71-9

phenyl isocyanate

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

1227407-95-5

1-methyl-6,8-dioxo-N,7-diphenyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,6-a]pyrimidine-9-carboxamide

Conditions
ConditionsYield
In acetonitrile at 20℃; Inert atmosphere; Reflux;71%
629-05-0

n-octyne

201230-82-2

carbon monoxide

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

1418740-37-0

7-hexyl-1,8a-dimethyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyriamidin-6(8aH)-one

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 80℃; under 60804.1 Torr; for 6h; Pauson-Khand Annulation; Autoclave;64%
5416-93-3

4-Methoxyphenyl isocyanate

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

1227407-97-7

N,7-bis(4-methoxyphenyl)-1-methyl-6,8-dioxo-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,6-a]pyrimidine-9-carboxamide

Conditions
ConditionsYield
In acetonitrile at 20℃; Inert atmosphere; Reflux;63%
1711-05-3

m-anisoyl chloride

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

1228685-33-3

2-[1-(3-methoxybenzoyl)-3-methyltetrahydropyrimidin-2(1H)-ylidene]-1,3-bis(3-methoxyphenyl)propane-1,3-dione

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Reflux;61%
201230-82-2

carbon monoxide

68274-83-9

5-hexyn-1-yl acetate

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

1418740-39-2

7-(4-acetoxy)butyl-1,8a-dimethyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyriamidin-6(8aH)-one

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 80℃; under 60804.1 Torr; for 6h; Pauson-Khand Annulation; Autoclave;61%
4265-16-1

2-formylbenzo[b]furan

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

109-94-4

formic acid ethyl ester

1-methyl-2-<(2-benzofuryl)vinyl>-1,4,5,6-tetrahydropyrimidine formate

Conditions
ConditionsYield
With lithium fluoride at 50℃; for 18h;52%
886-66-8

1,4-diphenyl-1,3-butadiyne

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

N-(2-(3,6-diphenylpyridin-2-yl)ethyl)-N-methylacetamide

Conditions
ConditionsYield
With carbon dioxide; water; caesium carbonate In acetonitrile at 80℃; for 48h; Reagent/catalyst; Schlenk technique;45%
86-81-7

3,4,5-trimethoxy-benzaldehyde

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

109-94-4

formic acid ethyl ester

1-methyl-2-<2-(3,4,5-trimethoxyphenyl)vinyl>-1,4,5,6-tetrahydropyrimidine formate

Conditions
ConditionsYield
With lithium fluoride at 50℃; for 18h;42%
5271-67-0

2-Thiophenecarbonyl chloride

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

2-(1-Methyl-tetrahydro-pyrimidin-2-ylidene)-1,3-di-thiophen-2-yl-propane-1,3-dione

Conditions
ConditionsYield
With triethylamine In acetonitrile Ambient temperature;40.5%
120-57-0

piperonal

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

109-94-4

formic acid ethyl ester

1-methyl-2-<2-(3,4-methylenedioxyphenyl)vinyl>-1,4,5,6-tetrahydropyrimidine formate

Conditions
ConditionsYield
With lithium fluoride at 50℃; for 18h;40%
4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

38818-50-7

4-chloro-3-nitro-benzoyl chloride

1,3-Bis-(4-chloro-3-nitro-phenyl)-2-(1-methyl-tetrahydro-pyrimidin-2-ylidene)-propane-1,3-dione

Conditions
ConditionsYield
With triethylamine In acetonitrile Ambient temperature;40%
5834-16-2

3-methyl-2-thiophenecarboxaldehdye

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

83467-08-7

1-methyl-2-<(3-methyl)thio-2-thenoyl methylene>hexahydropyrimidine

Conditions
ConditionsYield
With sulfur In xylene Heating; 5-8 h;37.8%
527-69-5

2-furancarbonyl chloride

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

1,3-Di-furan-2-yl-2-(1-methyl-tetrahydro-pyrimidin-2-ylidene)-propane-1,3-dione

Conditions
ConditionsYield
With triethylamine In acetonitrile Ambient temperature;37%
98-03-3

thiophene-2-carbaldehyde

4271-96-9

1,2-dimethyl-1,4,5,6-tetrahydropyrimidine

83467-07-6

1-methyl-2-(thio-2-thenoyl methylene)hexahydropyrimidine

Conditions
ConditionsYield
With sulfur In xylene Heating; 5-8 h;36.8%

1,2-Dimethyl-1,4,5,6-tetrahydropyrimidine Chemical Properties

Molecular Structure of 1,2-Dimethyl-1,4,5,6-tetrahydropyrimidine (CAS NO.4271-96-9):

IUPAC Name: 1,2-dimethyl-5,6-dihydro-4H-pyrimidine 
Empirical Formula: C6H12N2
Molecular Weight: 112.1729
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: 15.6 Å2
Index of Refraction: 1.513
Molar Refractivity: 34.28 cm3
Molar Volume: 113.9 cm3
Surface Tension: 31.4 dyne/cm
Density: 0.98 g/cm3
Flash Point: 69.8 °C
Enthalpy of Vaporization: 42.79 kJ/mol
Boiling Point: 191.7 °C at 760 mmHg
Vapour Pressure: 0.507 mmHg at 25°C
EINECS: 224-262-2
Product Categories: Boron, Nitrile, Thio,& TM-Cpds; Heterocyclic Compounds
InChI
InChI=1/C6H12N2/c1-6-7-4-3-5-8(6)2/h3-5H2,1-2H3
Smiles
N1=C(N(CCC1)C)C

1,2-Dimethyl-1,4,5,6-tetrahydropyrimidine Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 22-34
R22:Harmful if swallowed. 
R34:Causes burns.
Safety Statements: 23-26-36/37/39
S23:Do not breathe vapour. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: 3267

1,2-Dimethyl-1,4,5,6-tetrahydropyrimidine Specification

  1,2-Dimethyl-1,4,5,6-tetrahydropyrimidine , with CAS number of 4271-96-9, can be called pyrimidine, 1,4,5,6-tetrahydro-1,2-dimethyl- ; 1,4,5,6-tetrahydro-1,2-dimethylpyrimidine ; 2,3-Dimethyltetrahydropyrimidine .

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