p-Toluenesulfonic acid monohydrate → 1-(3-Bromomethyl 4-hydroxybutyl)-1H-pyrimidine-2,4-dione

HRID 908531Notes

Reaction equation

HRID 908531 reaction equation
[Br:1][CH2:2][CH:3]([CH2:14][O:15]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:4][CH2:5][N:6]1[CH:11]=[CH:10][C:9](=[O:12])[NH:8][C:7]1=[O:13].CC1C=CC(S(O)(=O)=O)=CC=1.O.C(Cl)(Cl)Cl.CO>CO>[Br:1][CH2:2][CH:3]([CH2:14][OH:15])[CH2:4][CH2:5][N:6]1[CH:11]=[CH:10][C:9](=[O:12])[NH:8][C:7]1=[O:13]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21584188Chloroform methanolHCID 594637601-(3-Bromomethyl-4-trityloxybutyl)-1H-pyrimidine-2,4-dione

Product 1

HCID 594637591-(3-Bromomethyl 4-hydroxybutyl)-1H-pyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound 37 (22 g, 0.042 mol) in methanol (100 mL) was treated with PTSA.H2O (0.80 g, 0.0042 mol) and stirred for 6 h at RT. The reaction mixture was concentrated under vacuum and the crude compound was used for next reaction (10.5 g, crude product). TLC: Chloroform/Methanol, 1:1, Rf=0.2

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe crude compound was used for next reaction (10.5 g, crude product)

Sources & evidence

ORD record
ord-d12c2bb14b3f4fc19f6c8a943760ace0
Source dataset
uspto-grants-2011_09
Patent number
US08017620B2

Reaction notes

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