(Cyclopropylmethyl)(2-methoxyethyl)amine → N-[4-(aminomethyl)phenyl]-6-[(cyclopropylmethyl)(2-methoxyethyl)amino]pyrimidine-4-carboxamide hydrochloride

HRID 1746762Notes

Reaction equation

HRID 1746762 reaction equation
[Cl:1][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.[CH:26]1([CH2:29][NH:30][CH2:31][CH2:32][O:33][CH3:34])[CH2:28][CH2:27]1>>[ClH:1].[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:30]([CH2:29][CH:26]3[CH2:28][CH2:27]3)[CH2:31][CH2:32][O:33][CH3:34])[N:7]=[CH:6][N:5]=2)=[O:9])=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 19353678(Cyclopropylmethyl)(2-methoxyethyl)amineHCID 59447092Tert-butyl (4-{[(6-chloropyrimidin-4-yl)carbonyl]amino}benzyl)carbamate2×

Product 1

HCID 68488865N-[4-(aminomethyl)phenyl]-6-[(cyclopropylmethyl)(2-methoxyethyl)amino]pyrimidine-4-carboxamide hydrochloride

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-(cyclopropylmethyl)-2-methoxyethanamine, the title compound was obtained as a pale yellow solid after purification by column chromatography (silica) eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-06dee23e55694b478b6fb1a47f4348b2
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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