6-Chloro-m-anisidine → 4-(2-Chloro-5-methoxyanilino)-2,6-di(2-pyridinyl)pyrimidine

HRID 1765213Notes

Reaction equation

HRID 1765213 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N:3]=1.[Cl:20][C:21]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:22]=1[NH2:23]>>[Cl:20][C:21]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:22]=1[NH:23][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N:3]=1

Participants

3

Reactant 2

HCID 754606-Chloro-m-anisidineHCID 27670664-Chloro-2,6-di(2-pyridinyl)pyrimidine

Product 1

HCID 227323954-(2-Chloro-5-methoxyanilino)-2,6-di(2-pyridinyl)pyrimidine

Procedure

The title compound was prepared from a mixture of 4-chloro-2,6-di(2-pyridinyl)pyrimidine (25 mg, 0.093 mmol) and 2-chloro-5-methoxyaniline (27 mg, 0.140 mmol) similar to Example 111 and isolated as a white solid (20 mg, 55%). 1H NMR (CDCl3): 8.87–8.82 (m, 1H), 8.72–8.64 (m, 3H), 8.08 (d, J=2.7 Hz, 1H), 7.92 (s, 1H), 7.90–7.86 (m, 2H), 7.45–7.38 (m, 3H), 7.33 (d, J=8.7 Hz, 1H), 6.67 (dd, J=3.0, 9.0 Hz, 1H), 3.91 (s, 3H).

Sources & evidence

ORD record
ord-a9f88a8b89ef43f7b88f21692f23051d
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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