Tert-butyl (3-(2-((4-carbamoylphenyl)amino)-4-(propylamino)pyrimidine-5-carboxamido)propyl)carbamate → 4-(Propylamino)pyrimidine-5-carboxamide

HRID 2284692Notes

Reaction equation

HRID 2284692 reaction equation
C(C1C=CC(N[C:11]2[N:16]=[C:15]([NH:17][CH2:18][CH2:19][CH3:20])[C:14]([C:21]([NH:23]CCCNC(=O)OC(C)(C)C)=[O:22])=[CH:13][N:12]=2)=CC=1)(=O)N>C(Cl)(Cl)Cl.CO.FC(F)(F)C(O)=O>[CH2:18]([NH:17][C:15]1[C:14]([C:21]([NH2:23])=[O:22])=[CH:13][N:12]=[CH:11][N:16]=1)[CH2:19][CH3:20]

Participants

5

Reactant 1

HCID 90052173Tert-butyl (3-(2-((4-carbamoylphenyl)amino)-4-(propylamino)pyrimidine-5-carboxamido)propyl)carbamate

Product 1

HCID 1317335334-(Propylamino)pyrimidine-5-carboxamideYield 385.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a suspension of tert-butyl (3-(2-((4-carbamoylphenyl)amino)-4-(propylamino)pyrimidine-5-carboxamido)propyl)carbamate (D2, 190 mg) in chloroform (8 mL) and methanol (2 mL), trifluoroacetic acid (1 mL) was added at room temperature, and the mixture was stirred at the same temperature for 30 minutes. The solvent was evaporated under reduced pressure to obtain N-(3-aminopropyl)-2-(4-carbamoylphenyl)amino)-4-(propylamino)pyrimidine-5-carboxamide (D3) trifluoroacetate (280 mg).

Workup

  1. additionwas added at room temperature
  2. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-be3a0c69a5e844c48b450b810b856544
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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