Potassium Carbonate → 4-[1-(1-Cyclopentylbut-3-yn-1-yl)-1H-pyrazol-4-yl]-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 1962807Notes

Reaction equation

HRID 1962807 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[CH:7]1([CH:12]([N:16]2[CH:20]=[C:19]([C:21]3[C:22]4[CH:29]=[CH:28][N:27]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:23]=4[N:24]=[CH:25][N:26]=3)[CH:18]=[N:17]2)[CH2:13][CH:14]=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO.O>[CH:7]1([CH:12]([N:16]2[CH:20]=[C:19]([C:21]3[C:22]4[CH:29]=[CH:28][N:27]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:35])[CH3:36])[C:23]=4[N:24]=[CH:25][N:26]=3)[CH:18]=[N:17]2)[CH2:13][C:14]#[CH:1])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574780313-Cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanalHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 574781104-[1-(1-Cyclopentylbut-3-yn-1-yl)-1H-pyrazol-4-yl]-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 962WaterSolvent

Procedure

To a mixture of potassium carbonate (38.4 mg, 0.278 mmol) in methanol (2.0 mL) at 0° C. was added a solution of 3-cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]propanal (prepared as in Example 727, step 4) (61.0 mg, 0.139 mmol) in methanol (1.0 mL), followed by a solution of dimethyl (1-diazo-2-oxopropyl)phosphonate (Tetrahedron, 62 (2006), pp 6673-6680) (40.0 mg, 0.208 mmol) in methanol (1.0 mL). The mixture was slowly warmed to ambient temperature and stirred for 16 hours. The mixture was then diluted with water and extracted with ethyl acetate. The combined extracts were washed with water, saturated ammonium chloride, and then dried over sodium sulfate and the solvent was removed in vacuo to afford the product, which was used without further purification (52 mg, 86%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with water, saturated ammonium chloride
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed in vacuo
  5. customto afford the product, which
  6. customwas used without further purification (52 mg, 86%)

Sources & evidence

ORD record
ord-56c1112abfeb4893a6d8fce0f84f2687
Source dataset
uspto-grants-2013_04
Patent number
US08415362B2

Reaction notes

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