Cyclopropanemethanamine, N-propyl- → N-[4-(aminomethyl)phenyl]-6-[(cyclopropylmethyl)(propyl)amino]pyrimidine-4-carboxamide

HRID 1946779Notes

Reaction equation

HRID 1946779 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:25]=[CH:24][C:14]([CH2:15][NH:16]C(=O)OC(C)(C)C)=[CH:13][CH:12]=2)=[O:9])[CH:3]=1.[CH2:26]([NH:29][CH2:30][CH:31]1[CH2:33][CH2:32]1)[CH2:27][CH3:28]>>[NH2:16][CH2:15][C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:8]([C:4]2[CH:3]=[C:2]([N:29]([CH2:30][CH:31]3[CH2:33][CH2:32]3)[CH2:26][CH2:27][CH3:28])[N:7]=[CH:6][N:5]=2)=[O:9])=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 117787Cyclopropanemethanamine, N-propyl-HCID 59447092Tert-butyl (4-{[(6-chloropyrimidin-4-yl)carbonyl]amino}benzyl)carbamate2×

Product 1

HCID 25182932N-[4-(aminomethyl)phenyl]-6-[(cyclopropylmethyl)(propyl)amino]pyrimidine-4-carboxamide

Procedure

Following the general method as outlined in Example 72 (Steps 1 and 2), starting from tert-butyl (4-{[(6-chloropyrimidin-4-yl)carbonyl]amino}benzyl)carbamate (Intermediate 22) and N-propylcyclopropanemethylamine (Aldrich), the title compound was obtained as a beige solid after purification by column chromatography (silica) eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-b294d9499870424d86d2ff9b582ca139
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Reaction notes

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