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

HRID 2284652Notes

Reaction equation

HRID 2284652 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:14][CH2:15][CH2:16][CH3:17])=[N:8][C:9](SC)=[N:10][CH:11]=1)=[O:5])[CH3:2].C([N:21](CC)C(C)C)(C)C.N.O>CN1CCCC1=O.ClC1C=CC=C(C(OO)=O)C=1>[NH2:21][C:9]1[N:8]=[C:7]([NH:14][CH2:15][CH2:16][CH3:17])[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:11][N:10]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 81531DiisopropylethylamineHCID 105629752-Methylthio-4-propylamino-5-pyrimidine carboxylic acid ethyl ester

Product 1

HCID 90052100Ethyl 2-amino-4-(propylamino)pyrimidine-5-carboxylate

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 70297m-Chloroperbenzoic acidSolvent

Procedure

To a solution of 2-(methylthio)-4-(propylamino)pyrimidine-5-carboxylic acid ethyl ester (A1, 11.7 g) in N-methylpyrrolidone (90 mL), meta-chloroperbenzoic acid (70 to 75% wt, 20.8 g) was added under ice cooling, and the mixture was stirred at room temperature for 40 minutes. To the reaction mixture, N,N-diisopropylethylamine (23.9 mL) and 10% aqueous ammonia (60.0 mL) were added at room temperature, and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was poured into water (400 mL). The solid matter was taken by filtration, washed with water, and then dried under reduced pressure to obtain ethyl 2-amino-4-(propylamino)pyrimidine-5-carboxylate (C3, 8.0 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hour
  2. filtrationThe solid matter was taken by filtration
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-1419957473094188ad1fcf531775181f
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

Loading…