m-Toluidine → 4-(3-Methylanilino)-6-methyl-2-(2-pyridinyl)pyrimidine

HRID 1765137Notes

Reaction equation

HRID 1765137 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=1>>[CH3:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[NH:15][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:3]=1

Participants

3

Reactant 2

HCID 7934m-ToluidineHCID 27633954-Chloro-6-methyl-2-(pyridin-2-yl)pyrimidine

Product 1

HCID 99654004-(3-Methylanilino)-6-methyl-2-(2-pyridinyl)pyrimidine

Procedure

The title compound was prepared from 4-chloro-6-methyl-2-(2-pyridinyl)pyrimidine (100 mg, 0.486 mmol) and m-toluidine (52 μl, 0.486 mmol) similar to Example 13 and isolated as a pale yellow oil (132 mg, 99%). 1H NMR (CDCl3): 8.76–8.74 (m, 1H), 8.43–8.40 (m, 1H), 7.78–7.72 (m, 1H), 7.55 (s, 1H), 7.31–7.08 (m, 4H), 6.92 (d, J=7.2 Hz, 1H), 6.55 (s, 1H), 2.41 (s, 3H), 2.30 (s, 3H).

Sources & evidence

ORD record
ord-d55e1f18ce724f928fa1d169f72d0701
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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