Water → Methyl 7-cyclopentyl-2-(methylthio)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate

HRID 79141Notes

Reaction equation

HRID 79141 reaction equation
[H-].[Na+].[CH:3]1([N:8]([C:14]2[C:19]([CH:20]=O)=[CH:18][N:17]=[C:16]([S:22][CH3:23])[N:15]=2)[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:7][CH2:6][CH2:5][CH2:4]1.O>CCCCCC.C1C=CC=CC=1>[CH:3]1([N:8]2[C:14]3[N:15]=[C:16]([S:22][CH3:23])[N:17]=[CH:18][C:19]=3[CH:20]=[C:9]2[C:10]([O:12][CH3:13])=[O:11])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 58299719Methyl 2-(cyclopentyl(5-formyl-2-(methylthio)pyrimidin-4-yl)amino)acetate

Product 1

HCID 58299712Methyl 7-cyclopentyl-2-(methylthio)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylateYield 34.8%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8058HexaneSolvent

Conditions

Temperature
70 °C

Procedure

Sodium hydride (3.85 g, 167 mmol) (freshly washed with hexane) was added to a solution of compound 226 (12.95 g, 41.9 mmol) in benzene (150 mL). The reaction was stirred at 70° C. After 1 h, the reaction contents were poured into water (300 mL) and extracted with ethyl acetate (2×100 mL). The combined organics were washed with brine, dried over MgSO4, and concentrated in vacuo. Silica gel chromatography (gradient elution 0 to 50% ethyl acetate in hexanes) afforded compound 227 (4.24 g, 34.8% yield).

Workup

  1. customthe reaction contents
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. washSilica gel chromatography (gradient elution 0 to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-934a3dcf4f314798a4474657b46590f3
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

Loading…