Water → 2,5-dichloro-N-(2-((1-methylethyl)sulfonyl)phenyl)-4-pyrimidinamine

HRID 1500458Notes

Reaction equation

[CH:1]([S:4]([C:7]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1[NH2:9])(=[O:6])=[O:5])([CH3:3])[CH3:2].[H-].[Na+].[Cl:16][C:17]1[N:22]=[C:21](Cl)[C:20]([Cl:24])=[CH:19][N:18]=1.O>CN(C=O)C>[Cl:16][C:17]1[N:22]=[C:21]([NH:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])[C:20]([Cl:24])=[CH:19][N:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 2-(isopropylsulfonyl)aniline (B-3) (32 g, 0.16 mol) in DMF (300 mL) at 0° C., was added NaH (13 g, 0.32 mol). After stirred at 0° C. for 0.5 h, 2,4,5-trichloropyrimidine (35 g, 0.13 mol) was dropwised to the mixture at 0° C. The solution was stirred for 12 h at RT, then poured into water, extracted with EtOAc, washed with water, brine, dried and concentrated. The residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (10:1 to 5:1) to give the title compound (B) as a yellow solid. MS-ESI (m/z): 346 (M+1)+.

Workup

customwas dropwised to the mixture at 0° C
stirringThe solution was stirred for 12 h at RT
extractionextracted with EtOAc
washwashed with water, brine
customdried
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (10:1 to 5:1)

Sources & evidence

ORD record: ord-5b02da86d51b4c8d8afc90dc472689d0
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206166B2

Reaction notes

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