HCID 18674970, compound → HCID 18674997, compound

HRID 1634911Notes

Reaction equation

[OH:1][CH2:2][C:3]1[C:4]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=2)=[N:5][C:6](SC)=[N:7][CH:8]=1>C(O)C.N.[Ni]>[OH:1][CH2:2][C:3]1[C:4]([C:11]2[CH:12]=[C:13]([O:21][CH3:22])[C:14]([O:19][CH3:20])=[C:15]([O:17][CH3:18])[CH:16]=2)=[N:5][CH:6]=[N:7][CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

5-Hydroxymethyl-2-methylthio-4-(3,4,5-trimethoxyphen yl)pyrimidine (1.75 g) was dissolved in a mixed solvent of ethanol (50 mL) and aqueous ammonia (5 mL). Raney nickel (R=100, wet type, 17.0 g) was added to the solution, and the mixture was stirred at 90° C. for 2.5 hours. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. Water was added to the residue to conduct extraction with ethyl acetate. The resultant organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1) to obtain the title compound.

Workup

filtrationThe reaction mixture was filtered through celite
concentrationthe filtrate was concentrated under reduced pressure
additionWater was added to the residue
extractionextraction with ethyl acetate
washThe resultant organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record: ord-a80f9442929447e2a3c9eaec19a289ad
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06509329B1

Reaction notes

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