5-Methoxy-o-toluidine → 4-(5-Methoxy-2-methylanilino)-2,6-di(2-pyridinyl)pyrimidine

HRID 2084157Notes

Reaction equation

HRID 2084157 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.[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([CH3:29])=[C:26]([CH:28]=1)[NH2:27]>>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([CH3:29])=[C:26]([CH:28]=1)[NH:27][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 995005-Methoxy-o-toluidineHCID 27670664-Chloro-2,6-di(2-pyridinyl)pyrimidine

Product 1

HCID 227324744-(5-Methoxy-2-methylanilino)-2,6-di(2-pyridinyl)pyrimidine

Procedure

The title compound was prepared from a mixture 4-chloro-2,6-di(2-pyridinyl)pyrimidine (25 mg, 0.093 mmol) and 5-methoxy-2-methylaniline (19 mg, 0.140 mmol) similar to Example 111 and isolated as a white solid (21 mg, 61%). 1H NMR (CDCl3): 8.88-8.86 (m, 1H), 8.71-8.60 (m, 3H), 7.92-7.83 (m, 2H), 7.62 (s, 1H), 7.44-7.34 (m, 2H), 7.22 (d, J=8.4 Hz, 1H), 7.08 (d, J=2.7 Hz, 1H), 7.06 (s, 1H), 6.78 (dd, J=2.4, 8.4 Hz, 1H), 3.82 (s, 3H), 2.52 (s, 3H).

Sources & evidence

ORD record
ord-43855379393642baba969a95672e9926
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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