Methane → Isopropyl 1,4,5,6-Tetrahydropyrimidine-5-carboxylate Hydrochloride

HRID 1681872Notes

Reaction equation

HRID 1681872 reaction equation
Cl.[NH:2]1[CH2:7][CH:6]([C:8]([OH:10])=[O:9])[CH2:5][N:4]=[CH:3]1.S(Cl)([Cl:13])=O.C.[CH3:16][CH:17](O)[CH3:18]>>[ClH:13].[NH:4]1[CH2:5][CH:6]([C:8]([O:10][CH:17]([CH3:18])[CH3:16])=[O:9])[CH2:7][N:2]=[CH:3]1

Participants

5

Reactant 4

HCID 297MethaneHCID 3776IsopropanolHCID 24386Thionyl ChlorideHCID 703421841,4,5,6-Tetrahydropyrimidine-5-carboxylic acid hydrochloride

Product 1

HCID 20080421Isopropyl 1,4,5,6-Tetrahydropyrimidine-5-carboxylate HydrochlorideYield 84%

Procedure

1,4,5,6-Tetrahydropyrimidine-5-carboxylic acid hydrochloride (1.0 g, 6.08 mmol) was suspended in 2-propanol (50 ml) and thionyl chloride (0.76 g, 6.39 mmol) was added dropwise. The resulting mixture was refluxed 24 h. The pink solution was treated with charcoal and then reduced in volume to 15 ml by evaporating unreacted alcohol. By allowing the solution to stand overnight, white crystals (1.08 g, 84%) were obtained in three crops, mp 170° C. 300 MHz nmr confirmed product. Microanalysis calc.: C 46.49, H 7.26, N 13.56, found: C 46.49, H 7.25, N 13.64.

Workup

  1. temperatureThe resulting mixture was refluxed 24 h
  2. customby evaporating unreacted alcohol

Sources & evidence

ORD record
ord-afbf09fa394c45db9eda9391e8260392
Source dataset
uspto-grants-1992_12
Patent number
US05175166

Reaction notes

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