Phenyl chloroformate → Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl ester

HRID 2051133Notes

Reaction equation

HRID 2051133 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.[C:12](Cl)(=[O:20])[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1.CN(C)C1C=CN=CC=1>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([O:10][CH3:11])[N:3]=[C:2]([NH:1][C:12](=[O:20])[O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:7]=1

Participants

5

Reactant 2

HCID 15891Phenyl chloroformateHCID 1189462-Amino-4,6-dimethoxypyrimidine

Product 1

HCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterYield 62.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8.0 g of 2-amino-4,6-dimethoxypyrimidine in 50 ml of tetrahydrofuran are added 4.0 g of phenyl chlorocarbonate and 0.1 g of 4-dimethylaminopyridine, followed by stirring for 17 hours at room temperature. The mixture is allowed to stand overnight and filtered to remove insoluble product and the filtrate is purified by silica gel chromatography (eluent: dichloromethane) to give 4.4 g of the title compound. mp. 118°-119° C.

Workup

  1. waitto stand overnight
  2. filtrationfiltered
  3. customto remove insoluble product
  4. customthe filtrate is purified by silica gel chromatography (eluent: dichloromethane)

Sources & evidence

ORD record
ord-4e95f08da92448d6bd81c903a7d4b713
Source dataset
uspto-grants-1991_05
Patent number
US05017212

Reaction notes

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