3-Amino-p-cresol → 4-(5-Hydroxy-2-methylanilino)-2-(2-pyridinyl)-6-trifluoromethylpyrimidine

HRID 1765282Notes

Reaction equation

HRID 1765282 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:3]=1.[OH:18][C:19]1[CH:20]=[CH:21][C:22]([CH3:26])=[C:23]([CH:25]=1)[NH2:24]>>[OH: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]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:3]=1

Participants

3

Reactant 2

HCID 178203-Amino-p-cresolHCID 113115004-Chloro-2-(2-pyridinyl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 227323984-(5-Hydroxy-2-methylanilino)-2-(2-pyridinyl)-6-trifluoromethylpyrimidine

Procedure

The title compound was prepared from 4-chloro-2-(2-pyridinyl)-6-trifluoromethylpyrimidine (40 mg, 0.154 mmol) and 5-hydroxy-2-methylaniline (28 mg, 0.231 mmol) similar to example 185 and was isolated as a pale solid (40 mg, 75%). 1H NMR (CDCl3): 9.73 (m, 1H), 8.44–8.41 (m, 1H), 7.81–7.75 (m, 1H), 7.46 (s, 1H), 7.34–7.28 (m, 2H), 7.23 (t, J=0.1 Hz, 1H), 7.09–7.06 (m, 1H), 7.00–6.97 (m, 1H), 6.55 (d, J=0.6 Hz, 1H), 2.44 (s, 3H), 2.43 (d, J=0.6, 3H).

Sources & evidence

ORD record
ord-045f96637aed4080ab1346c9eb62a0b3
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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