5-Methoxy-o-toluidine → 4-(5-Methoxy-2-methylanilino)-6-(methoxymethyl)-2-(2-methyl-1,3-thiazol-4-yl)pyrimidine

HRID 2084103

Reaction equation

HRID 2084103 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][O:9][CH3:10])[N:5]=[C:4]([C:11]2[N:12]=[C:13]([CH3:16])[S:14][CH:15]=2)[N:3]=1.[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([CH3:26])=[C:23]([CH:25]=1)[NH2:24]>>[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([CH3:26])=[C:23]([CH:25]=1)[NH:24][C:2]1[CH:7]=[C:6]([CH2:8][O:9][CH3:10])[N:5]=[C:4]([C:11]2[N:12]=[C:13]([CH3:16])[S:14][CH:15]=2)[N:3]=1

Participants

3

Reactant 2

HCID 995005-Methoxy-o-toluidineHCID 27995334-Chloro-6-(methoxymethyl)-2-(2-methyl-1,3-thiazol-4-yl)pyrimidine

Product 1

HCID 99467624-(5-Methoxy-2-methylanilino)-6-(methoxymethyl)-2-(2-methyl-1,3-thiazol-4-yl)pyrimidine

Procedure

The title compound was prepared from a mixture of 4-chloro-6-(methoxymethyl)-2-(2-methyl-1,3-thiazol-4-yl)pyrimidine (50 mg, 0.196 mmol) and 5-methoxy-2-methylaniline (27 mg, 0.196 mmol) similar to Example 13 and isolated as a tan oil (42 mg, 60%). 1H NMR (CDCl3): 8.12 (s, 1H), 7.19 (d, J=8.4 Hz, 1H), 6.99 (d, J=2.4 Hz, 1H), 6.89 (s, 1H), 6.75 (dd, J=3.0, 8.7 Hz, 1H), 6.56 (s, 1H), 4.50 (s, 2H), 3.80 (s, 3H), 3.44 (s, 3H), 2.83 (s, 3H), 2.21 (s, 3H).

Sources & evidence

ORD record
ord-9240fa195727474c83af852cdccbaff3
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Linked notes

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