N-Methylbenzeneethanamine → 2-(N-methylphenethylamino)-6-phenylpyrimidine-4-carboxamide

HRID 68299

Reaction equation

CS([C:5]1[N:10]=[C:9]([C:11]([NH2:13])=[O:12])[CH:8]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:6]=1)(=O)=O.CCN(C(C)C)C(C)C.[CH3:29][NH:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O1CCOCC1>[CH3:29][N:30]([CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:5]1[N:10]=[C:9]([C:11]([NH2:13])=[O:12])[CH:8]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:6]=1

Participants

Conditions

Temperature: 85 °C

Procedure

2-Methanesulfonyl-6-phenylpyrimidine-4-carboxamide (70 mg, 0.25 mmol), 1,4-dioxane (4 mL), DIPEA (0.3 mL, 2.0 mmol) and N-methylphenethylamine (82 mg, 0.6 mmol) were added to a 8 mL vial. The vial was sealed and heated at 85° C. for two days. The reaction mixture was allowed to cool to room temperature, and the solvent then removed by centrifugal evaporation. The residue was purified by preparative HPLC to afford 43 mg of 2-(N-methylphenethylamino)-6-phenylpyrimidine-4-carboxamide. 1H NMR (CDCl3, 300 MHz) δ 8.14 (m, 2H), 7.74 (s, 1H), 7.67 (br s, 1H), 7.47 (m, 3H), 7.25 (m, 5H), 5.79 (br s, 1H), 3.95 (t, J=6.9 Hz, 2H), 3.21 (s, 3H), 2.97 (t, J=6.9 Hz, 2H). HPLC ret. time 3.25 min, 10-100% CH3CN, 5 min run. ESI-MS m/z 333.3 (M+H)+.

Workup

customThe vial was sealed
temperatureto cool to room temperature
customthe solvent then removed by centrifugal evaporation
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-0539cb802972482dbf0f1709587fadb3
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822451B2

Linked notes

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