4-(Trifluoromethyl)aniline → HCID 22060490, compound

HRID 1932203Notes

Reaction equation

HRID 1932203 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[F:10][C:11]([F:20])([F:19])[C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1>>[F:10][C:11]([F:19])([F:20])[C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:2]2[N:7]=[C:6]([NH:16][C:15]3[CH:17]=[CH:18][C:12]([C:11]([F:10])([F:19])[F:20])=[CH:13][CH:14]=3)[C:5]([F:9])=[CH:4][N:3]=2)=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 22060490HCID 22060490, compound

Procedure

In a manner similar to the preparation of N2-N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidineamine, the reaction of 2,4-dichloro-5-fluoropyrimidine with 4-trifluoromethylaniline gave N2,N4-bis(4-trifluoromethylphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 8.06 (bs, 1H), 7.75 (d, 2H, J=9 Hz), 7.67 (d, 2H, J=9 Hz), 7.63 (d, 2H, J=9 Hz), 7.54 (d, 2H, J=9 Hz), 7.19 (bs, 1H), 6.96 (s, 1H); 19F NMR (CDCl3): δ −17598 (s, 3F), −17676 (s, 3F), −46549 (s, 1F); HPLC: 85% pure.

Sources & evidence

ORD record
ord-6b58f6a3d9504a2f86b2b49d18f034e8
Source dataset
uspto-grants-2012_05
Patent number
US08188276B2

Reaction notes

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