3-Amino-4-chlorophenol → 4-(2-Chloro-5-hydroxyanilino)-2-(2-pyridinyl)-6-trifluoromethylpyrimidine

HRID 2084231Notes

Reaction equation

HRID 2084231 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.[Cl:18][C:19]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][C:20]=1[NH2:21]>>[Cl:18][C:19]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][C:20]=1[NH:21][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 50700783-Amino-4-chlorophenolHCID 113115004-Chloro-2-(2-pyridinyl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 227324464-(2-Chloro-5-hydroxyanilino)-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 2-chloro-5-hydroxyaniline (30 mg, 0.231 mmol) similar to Example 185 and was isolated as an off white solid (15 mg, 28%). 1H NMR (DMSO-d6): 9.89 (s, 1H), 9.85 (brs, NH), 8.74(d, J=5.7, 1H), 8.22 (d, J=7.8 Hz, 1H), 7.97 (ddd, J=1.8, 5.7, 7.8 Hz, 1H), 7.54 (ddd, J=4.5, 6.0, 7.8 Hz, 1H), 7.35 (m, 2H), 7.19 (s, 1 H), 6.70 (dd, J=2.7, 5.7 Hz, 1H).

Sources & evidence

ORD record
ord-60b8c7e602784259ac16fae0dfe4f215
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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