Water → HCID 90051749, compound

HRID 2284707Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][CH3:18])[C:12]([CH2:19][S:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-])=O)[CH:22]=3)=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[Sn](Cl)Cl.O>C(O)C.C(OCC)(=O)C>[NH2:27][C:23]1[CH:22]=[C:21]([S:20][CH2:19][C:12]2[C:13]([NH:15][CH2:16][CH2:17][CH3:18])=[N:14][C:9]([NH:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:10][CH:11]=2)[CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of N2-(3-fluorophenyl)-5-(((3-nitrophenyl)thio)methyl)-N4-propylpyrimidine-2,4-diamine (E19, 160 mg) in ethanol (4 mL) and ethyl acetate (8 mL), tin(II) chloride (739 mg) was added at room temperature, and the mixture was stirred at 70° C. for 1 hour. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added to the mixture. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 5-(((3-aminophenyl)thio)methyl)-N2-(3-fluorophenyl)-N4-propylpyrimidine-2,4-diamine (E20).

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe organic layer was separated
washwashed successively with water and saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-9d223ba9bd3f4fc7819d68510ac6629e
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145415B2

Reaction notes

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