Tetrabutylammonium Fluoride → 4-chloro-6-(1-methyl-1H-[1,2,3]triazol-4-yl)-thieno[3,2-d]pyrimidine

HRID 1818945Notes

Reaction equation

HRID 1818945 reaction equation
[Cl:1][C:2]1[C:3]2[S:10][C:9]([C:11]3[N:12]=[N:13][N:14]([CH2:16][Si](C)(C)C)[CH:15]=3)=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[Cl:1][C:2]1[C:3]2[S:10][C:9]([C:11]3[N:12]=[N:13][N:14]([CH3:16])[CH:15]=3)=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 866031744-chloro-6-(1-trimethylsilanylmethyl-1H-[1,2,3]triazol-4-yl)-thieno[3,2-d]pyrimidine

Product 1

HCID 860949814-chloro-6-(1-methyl-1H-[1,2,3]triazol-4-yl)-thieno[3,2-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 48.3 (0.5 mmol) in THF (10.0 mL) was added several drops of water and TBAF (0.55 mmol; 1.0 M in THF) at 0° C. The resulting mixture was stirred at 0° C. for 15 minutes, concentrated and washed with hexanes. The white solid that formed was suspended in ice water (10 mL), filtered, washed with ice water and dried in vacuo to provide 4-chloro-6-(1-methyl-1H-[1,2,3]triazol-4-yl)-thieno[3,2-d]pyrimidine (compound 48.4) in 95% yield. EIMS (m/z): calcd. for C9H6ClN5S (M+)+H 252.00. found 252.00.

Workup

  1. concentrationconcentrated
  2. washwashed with hexanes
  3. customThe white solid that formed
  4. filtrationfiltered
  5. washwashed with ice water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-6c5d0022afdd4b6da47f920f44fb840e
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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