Water → Ethyl 2-((phenoxycarbonyl)amino)-4-(propylamino)pyrimidine-5-carboxylate

HRID 2284697Notes

Reaction equation

HRID 2284697 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][N:3]=1.N1C=CC=CC=1.O.Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:26]>CN(C)C=O>[O:27]([C:25]([NH:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][N:3]=1)=[O:26])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049Pyridine2×HCID 15891Phenyl chloroformate2×HCID 90052100Ethyl 2-amino-4-(propylamino)pyrimidine-5-carboxylate

Product 1

HCID 90052190Ethyl 2-((phenoxycarbonyl)amino)-4-(propylamino)pyrimidine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 2-amino-4-(propylamino)pyrimidine-5-carboxylate (C3, 5.00 g) and pyridine (2.2 mL) in N,N-dimethylformamide (45 mL), phenyl chloroformate (3.1 mL) was added dropwise under ice cooling, and the mixture was stirred at the same temperature for 40 minutes. To the reaction mixture, pyridine (1.0 mL) and phenyl chloroformate (1.5 mL) were added under ice cooling, and the mixture was stirred at the same temperature for 40 minutes. The reaction mixture was poured into water. The solid matter was taken by filtration, and dried under reduced pressure to obtain ethyl 2 -((phenoxycarbonyl)amino)-4-(propylamino)pyrimidine-5-carboxylate (E7, 2.89 g) as white solid.

Workup

  1. stirringthe mixture was stirred at the same temperature for 40 minutes
  2. filtrationThe solid matter was taken by filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-437e5d97fada4787a77ab836aa6cb911
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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