Tetrabutylammonium Fluoride → 4-Chloro-6-ethynylthieno[3,2-d]pyrimidine

HRID 1818943Notes

Reaction equation

HRID 1818943 reaction equation
[Cl:1][C:2]1[C:3]2[S:10][C:9]([C:11]#[C:12][Si](C)(C)C)=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:1][C:2]1[C:3]2[S:10][C:9]([C:11]#[CH:12])=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 858432224-Chloro-6-trimethylsilanylethynyl-thieno[3,2-d]pyrimidine

Product 1

HCID 599822624-Chloro-6-ethynylthieno[3,2-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 48.1 (5.0 mmol) in THF (50 mL) was tetrabutylammonium fluoride (“TBAF”; 5.0 mmol; 1.0 M in THF) at 0° C. After stirring at 0° C. for 5 minutes, the reaction mixture was concentrated, diluted with EtOAc, washed with saturated sodium bicarbonate, brine and dried. The solvent was removed and the residue purified by flash column chromatography on silica gel to provide 4-chloro-6-ethynyl-thieno[3,2-d]pyrimidine (compound 48.2) in 92% yield. EIMS (m/z): calcd. for C8H3ClN2S (M+)+H 194.97. found 195.00.

Workup

  1. customat 0° C
  2. concentrationthe reaction mixture was concentrated
  3. additiondiluted with EtOAc
  4. washwashed with saturated sodium bicarbonate, brine
  5. customdried
  6. customThe solvent was removed
  7. customthe residue purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-fe66d433a44c4667b202a6e8d62a482d
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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