Methanol → 2-(4-Sulphamoylanilino)-4-[2-fluoro-5-methyl-n-(4,4,4-trifluorobutyl)anilino]pyrimidine

HRID 860757Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]([CH2:17][CH2:18][CH2:19][C:20]([F:23])([F:22])[F:21])[C:9]2[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=2[F:16])[CH:5]=[CH:4][N:3]=1.[S:24]([NH2:34])(=[O:33])([C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1)=[O:25].CO>C(O)CCC>[S:24]([C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:2]2[N:7]=[C:6]([N:8]([CH2:17][CH2:18][CH2:19][C:20]([F:23])([F:22])[F:21])[C:9]3[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=3[F:16])[CH:5]=[CH:4][N:3]=2)=[CH:28][CH:27]=1)(=[O:25])(=[O:33])[NH2:34]

Participants

Conditions

Temperature: 95 °C

Procedure

2-Chloro-4-(N-4,4,4,-trifluorobutyl-2-fluoro-5-methylanilino)pyrimidine (215 mg, 0.62 mmol) was dissolved in n-butanol (2 ml) and sulphanilamide (85 mg, 0.50 mmol) was added. The resulting suspension was treated with methanol until all the solid dissolved. The reaction mixture was heated at 95° C. for 12 hours and allowed to cool to ambient temperature. The solid that had precipitated was collected by filtration, washed with a small volume of methanol and dried in vacuo to yield a white solid (132 mg). NMR (400 MHz@373K): 1.85 (m, 2H), 2.31 (m, 2H), 2.35 (s, 3H), 3.97 (t, 2H), 6.04 (d, 1H), 7.29 (m, 3H) 8.02 (d, 1H), 10.00 (br s, 1H); MS (M+H)+: 484.4.

Workup

dissolutiondissolved
temperatureto cool to ambient temperature
customThe solid that had precipitated
filtrationwas collected by filtration
washwashed with a small volume of methanol
customdried in vacuo

Sources & evidence

ORD record: ord-10c4457f1712401e966c1ebf3dfeb9c9
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153964B2

Reaction notes

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