HCID 68548926, compound → N-[4-(4-fluorophenyl)-5-[(E)-3-oxoprop-1-enyl]-6-propan-2-ylpyrimidin-2-yl]-N-methylmethanesulfonamide

HRID 1510825Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH2:14]/[CH:15]=[CH:16]/[OH:17])=[C:12]([CH:18]([CH3:20])[CH3:19])[N:11]=[C:10]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])[N:9]=2)=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13](/[CH:14]=[CH:15]/[CH:16]=[O:17])=[C:12]([CH:18]([CH3:20])[CH3:19])[N:11]=[C:10]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])[N:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

3-[4-(4-Fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl](2E)-propen-1-ol-(5 g) was dissolved in toluene (50 ml) at 25° C. and manganese dioxide (20 g) was added to it. The reaction mixture was stirred for 5 h at 25° C. After completion of the reaction, reaction mixture was filtered through hyflo and toluene was evaporated under reduced pressure at 40° C. to obtain the product as a semi solid. The product was further crystallized from hexane-ethyl acetate (20 ml, 9:1 v/v) (Yield: 4.8 g).

Workup

customAfter completion of the reaction, reaction mixture
filtrationwas filtered through hyflo and toluene
customwas evaporated under reduced pressure at 40° C.
customto obtain the product as a semi solid
customThe product was further crystallized from hexane-ethyl acetate (20 ml, 9:1 v/v) (Yield: 4.8 g)

Sources & evidence

ORD record: ord-f2c14ac5b405458da19a17fe5f8040c0
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08212034B2

Reaction notes

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