2,6-Difluoroaniline → HCID 24794484, compound

HRID 2251075Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4-chloro-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (10.0 g, 43.1 mmol) in acetonitrile (107 mL) is added 2,6-difluoroaniline (9.3 mL, 86.2 mmol). The mixture is heated to 90° C. for 4 hours. The reaction is cooled to room temperature and stored at 0° C. for 15 hours. The white precipitate which forms is filtered and washed with 20% EtOAc/hexanes to afford 14.3 g of the desired product which is used without further purification: 1H NMR (300 MHz, CDCl3/MeOH) δ 9.70 (s, 1H), 8.20 (s, 1H), 7.82 (s, 2H), 5.23 (s, 2H), 3.18 (s, 3H), 2.25 (s, 3H); ESI+ MS: m/z (rel intensity) 326.0 (100, M++H).

Workup

temperatureThe reaction is cooled to room temperature
filtrationThe white precipitate which forms is filtered
washwashed with 20% EtOAc/hexanes

Sources & evidence

ORD record: ord-b6975e9a76dd482889f41c0b1b697200
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319102B1

Reaction notes

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