Triethylamine → 7-Methylthieno[3,2-d]pyrimidine

HRID 1750875Notes

Reaction equation

HRID 1750875 reaction equation
Cl[C:2]1[C:3]2[S:10][CH:9]=[C:8]([CH3:11])[C:4]=2[N:5]=[CH:6][N:7]=1.C(N(CC)CC)C>CO.[OH-].[OH-].[Pd+2]>[CH3:11][C:8]1[C:4]2[N:5]=[CH:6][N:7]=[CH:2][C:3]=2[S:10][CH:9]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 27775864-Chloro-7-methylthieno(3,2-d)pyrimidine

Product 1

HCID 552806237-Methylthieno[3,2-d]pyrimidineYield 85.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

4-chloro-7-methyl-thieno[3,2-d]pyrimidine (6.5 g, 35.2 mmol) was dissolved in methanol (200 mL), added with Pd(OH)2 (1.3 g) and triethylamine (4.9 mL, 35.2 mmoL), and stirred for 5 hours under hydrogen pressure conditions. The reaction mixture was filtered through a Celite pad under reduced pressure, and concentrated. The concentrated compound was purified using silica gel chromatography (ethyl acetate:hexane=1:1 (v/v=1/1)) to obtain the title compound (4.5 g, 85%).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad under reduced pressure
  2. concentrationconcentrated
  3. customThe concentrated compound was purified

Sources & evidence

ORD record
ord-93b13e3f618f4ca4a9184d02470153fc
Source dataset
uspto-grants-2015_10
Patent number
US09156852B2

Reaction notes

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