Methanol → 1,4,5,6-Tetrahydro-5-methoxycarbonylpyrimidine Hydrochloride

HRID 1681874Notes

Reaction equation

HRID 1681874 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.[CH3:15]O>>[ClH:13].[CH3:15][O:9][C:8]([CH:6]1[CH2:7][NH:2][CH:3]=[N:4][CH2:5]1)=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 703421841,4,5,6-Tetrahydropyrimidine-5-carboxylic acid hydrochloride

Product 1

HCID 199620591,4,5,6-Tetrahydro-5-methoxycarbonylpyrimidine HydrochlorideYield 60%

Procedure

1,4,5,6-Tetrahydropyrimidine-5-carboxylic acid hydrochloride (6.34 g, 38.5 mmol) was dissolved in anhydrous methanol (200 ml) with stirring, and thionyl chloride (2.74 ml, 38.5 mmol) was added dropwise. The resulting solution was refluxed with stirring for 18 hours, then evaporated in vacuo to white solids. The crude product was recrystallized from anhydrous methanol to yield 4.12 g (60%) white crystals, mp 160°-164° C. Calculated: C 40.34, H 6.21, N 15.69; found: C 40.17, H 6.41, N 15.73.

Workup

  1. temperatureThe resulting solution was refluxed
  2. stirringwith stirring for 18 hours
  3. customevaporated in vacuo to white solids
  4. customThe crude product was recrystallized from anhydrous methanol

Sources & evidence

ORD record
ord-c6f40c0b42de4364921c20957ef382f6
Source dataset
uspto-grants-1992_12
Patent number
US05175166

Reaction notes

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