4-Aminophenol → 6-(cyclopentylamino)-N-(4-hydroxyphenyl)pyrimidine-4-carboxamide

HRID 1746689Notes

Reaction equation

HRID 1746689 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]=[CH:11][N:10]=[C:9]([C:13]([OH:15])=O)[CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1>C(#N)C>[CH:1]1([NH:6][C:7]2[N:12]=[CH:11][N:10]=[C:9]([C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)=[O:15])[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 594470556-(Cyclopentylamino)pyrimidine-4-carboxylic acid2×

Product 1

HCID 251826236-(cyclopentylamino)-N-(4-hydroxyphenyl)pyrimidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the general method as outlined in Example 1, starting from 6-[(cyclopentyl)amino]pyrimidine-4-carboxylic acid (Intermediate 5) and 4-aminophenol (Aldrich), the title compound was obtained as a yellow solid after trituration in acetonitrile. 1H NMR (300MHz, DMSO-d6) δ [ppm] 10.22 (1H, s), 9.32 (1H, s), 8.52 (1H, s), 7.85 (1H, d, J=7.0 Hz), 7.62 (2H, d, J=9.0 Hz), 7.13 (1H, s), 6.72 (2H, d, J=9.0 Hz), 4.28 (1H, m), 1.94 (2H, m), 1.74-1.40 (6H, m). MS (ESI+): 299.1. HPLC (Condition A): Rt 2.17 min (HPLC purity 96.6%).

Sources & evidence

ORD record
ord-ae016fa6377c4f8ba458257686add8b3
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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