2,3-Dimethoxyaniline → 4-(2,3-Dimethoxyanilino)-6-methyl-2-(2-pyridinyl)pyrimidine

HRID 2084081Notes

Reaction equation

HRID 2084081 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.[CH3:15][O:16][C:17]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19]>>[CH3:15][O:16][C:17]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[CH:20][C:18]=1[NH:19][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 2396032,3-DimethoxyanilineHCID 27633954-Chloro-6-methyl-2-(pyridin-2-yl)pyrimidine

Product 1

HCID 227324954-(2,3-Dimethoxyanilino)-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 2,3-dimethoxyaniline (69 μl, 0.486 mmol) similar to Example 11 and isolated as a white solid (169 mg). 1H NMR (CDCl3): 8.85-8.82 (m, 1H), 8.48 (d, J=7.8 Hz, 1H), 7.87-7.82 (m, 1H), 7.54 (d, J=7.5 Hz, 1H), 7.40-7.35 (m, 2H), 7.10 (t, J=8.4 Hz, 1H), 6.73 (d, J=1.5 Hz, 1H), 7.00 (s, 1H), 3.90 (s, 3H), 3.86 (s, 3H), 2.53 (s, 3H).

Sources & evidence

ORD record
ord-bb7fe81180474d03ab4ac4633af2f1ae
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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