Benzyl chloroformate → (Tetrahydro-2-oxo-1(2H)-pyrimidinyl)carbamic acid, phenylmethyl ester

HRID 2351088Notes

Reaction equation

HRID 2351088 reaction equation
Cl.[NH2:2][N:3]1[CH2:8][CH2:7][CH2:6][NH:5][C:4]1=[O:9].[CH2:10]([O:17][C:18](Cl)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O.O1CCCC1>[O:9]=[C:4]1[NH:5][CH2:6][CH2:7][CH2:8][N:3]1[NH:2][C:18](=[O:19])[O:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 1317161453-Aminotetrahydro-2(1H)-pyrimidinone, monohydrochloride

Product 1

HCID 54188774(Tetrahydro-2-oxo-1(2H)-pyrimidinyl)carbamic acid, phenylmethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Aminotetrahydro-2(1H)-pyrimidinone, monohydrochloride (30 g, 0.198 mol) was dissolved in a mixture of 240 ml water and 200 ml tetrahydrofuran. The pH was adjusted to 8.5 and benzylchloroformate (33.8 g, 0.198 mmol) was added dropwise while keeping the pH between 8 and 9. After the pH remained constant, the mixture was stirred for an additional hour. The tetrahydrofuran was removed in vacuo and the resulting crystals were filtered off with suction, triturated with ether and dried in vacuo. Yield 35.6 g, melting point 161°-163° C.

Workup

  1. additionwas added dropwise
  2. customThe tetrahydrofuran was removed in vacuo
  3. filtrationthe resulting crystals were filtered off with suction
  4. customtriturated with ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-d5cfc8e65e5e45c1bd812405d8b4536c
Source dataset
uspto-grants-1989_10
Patent number
US04871841

Reaction notes

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