Carbon tetrabromide → HCID 60209911, compound

HRID 1433100Notes

Reaction equation

HRID 1433100 reaction equation
O[CH2:2][C:3]1[CH:4]=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:31]>C1C=CC=CC=1>[Br:31][CH2:2][C:3]1[CH:4]=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22050485(2-(Methylsulfanyl)pyrimidin-5-yl)methanol

Product 1

HCID 60209911HCID 60209911, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5-hydroxymethyl-2-methylthiopyrimidine (0.1 g, 0.61 mmol), triphenylphosphine (0.45 g, 1.7 mmol) and carbon tetrabromide (0.28 g, 0.85 mmol) are stirred in benzene (5 mL) for 24 h. The mixture is evaporated and the residue is purified by flash chromatography (silica gel, 4:1 hexanes/ethyl acetate) to provide the intermediate title compound as a white solid (0.08 g, 61%). MS (ES), 219/221 [M+H]+ (Br).

Workup

  1. customThe mixture is evaporated
  2. customthe residue is purified by flash chromatography (silica gel, 4:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-e5c24fd45b004b6bb157294d4c716446
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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