Carbon tetrabromide → 1-(3-Bromomethyl-4-trityloxybutyl)-1H-pyrimidine-2,4-dione

HRID 1713376Notes

Reaction equation

HRID 1713376 reaction equation
O[CH2:2][CH:3]([CH2:14][O:15][C:16]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:4][CH2:5][N:6]1[CH:11]=[CH:10][C:9](=[O:12])[NH:8][C:7]1=[O:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:55].C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:55][CH2:2][CH:3]([CH2:14][O:15][C:16]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:4][CH2:5][N:6]1[CH:11]=[CH:10][C:9](=[O:12])[NH:8][C:7]1=[O:13]

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 594637571-(3-Hydroxymethyl-4-trityloxybutyl)-1H-pyrimidine-2,4-dione

Product 1

HCID 594637601-(3-Bromomethyl-4-trityloxybutyl)-1H-pyrimidine-2,4-dioneYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 36 (33 g, 0.073 mol) in dry DMF (200 mL) was added triphenylphosphine (29 g, 0.11 mol) with vigorous stirring at RT. The reaction mixture was cooled to 0° C., added CBr4 (36 g, 0.11 mol) portion wise over a period of 30 min and allowed to stir at RT for 24 h. The reaction mixture was cooled to 0° C., added saturated NaHCO3 solution (100 mL) and extracted with ethyl acetate (4×150 mL). The combined organic layer was dried, concentrated under vacuum and the crude product was purified by column chromatography on silica gel (50% ethyl acetate in hexane) to give the title compound (22 g, 57%). TLC: 100% EtOAc, Rf=0.7

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringto stir at RT for 24 h
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. extractionextracted with ethyl acetate (4×150 mL)
  5. customThe combined organic layer was dried
  6. concentrationconcentrated under vacuum
  7. customthe crude product was purified by column chromatography on silica gel (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-26c10fc73c7c4fbc804e6a548f6c3cd3
Source dataset
uspto-grants-2010_09
Patent number
US07795270B2

Reaction notes

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