Water → HCID 178527903, compound

HRID 1264162Notes

Reaction equation

HRID 1264162 reaction equation
[Br:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10](Cl)[C:5]=2[S:4][CH:3]=1.O.[SH-:13].[Na+].CN1CCCC1=O.O>C(OCC)(=O)C>[Br:1][C:2]1[C:6]2[N:7]=[CH:8][NH:9][C:10](=[S:13])[C:5]=2[S:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 16211346Sodium hydrosulfide hydrateHCID 166552667-Bromo-4-chlorothieno[3,2-d]pyrimidine

Product 1

HCID 178527903HCID 178527903, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-bromo-4-chlorothieno[3,2-d]pyrimidine (see below for preparation) (2.0 g), sodium hydrosulfide hydrate (0.66 g) and N-methylpyrrolidinone (10 ml) was heated at 102° C. for 1 hour. Water (500 ml) and ethyl acetate (500 ml) were added and stirred for 1 hour. The layers were separated and the aqueous phase extracted with ethyl acetate (300 ml). The combined organic extracts were washed with brine (300 ml), dried (MgSO4), treated with activated charcoal, then filtered through a silica pad and the solvent removed to give the title product, m.p. 328° C.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase extracted with ethyl acetate (300 ml)
  3. washThe combined organic extracts were washed with brine (300 ml)
  4. dry with materialdried (MgSO4)
  5. additiontreated with activated charcoal
  6. filtrationfiltered through a silica pad
  7. customthe solvent removed

Sources & evidence

ORD record
ord-c22818417d01491c9ba2dc41c49a0936
Source dataset
uspto-grants-2003_04
Patent number
US06541630B1

Reaction notes

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