(Dimethyl sulfide)trihydroboron → HCID 178518547, compound

HRID 474612Notes

Reaction equation

HRID 474612 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][S:16][C:17]3[NH:18][CH:19]=[C:20]([C:24](OCC)=[O:25])[C:21](=[O:23])[N:22]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].B.CSC>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:15][S:16][C:17]3[NH:18][CH:19]=[C:20]([CH2:24][OH:25])[C:21](=[O:23])[N:22]=3)=[CH:13][CH:14]=2)=[CH:4][C:3]=1[C:29]([F:30])([F:32])[F:31]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 178469905HCID 178469905, compound

Product 1

HCID 178518547HCID 178518547, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 2-{[(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)methyl]thio}-4-oxo-1,4-dihydro-5-pyrimidinecarboxylate (2.36 g, 4.87 mmol) in dry THF (20 mL) was added borane-methyl sulfide complex (2.0M in toluene) (7.30 mL, 14.60 mmol) dropwise under argon at 0° C. The mixture was stirred at 0° C. for 0.5 h, and warmed to room temperature for 1 h, then quenched with acetone. Purification via reverse phase flash chromatography then afforded the title compound (921 mg, 2.080 mmol, 42.7% yield). LCMS: rt=3.28 min, [M+H+]=443

Workup

  1. temperaturewarmed to room temperature for 1 h
  2. customquenched with acetone
  3. customPurification via reverse phase flash chromatography

Sources & evidence

ORD record
ord-3d4ffb16c26d4d978cdbededfeb2e7c9
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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