Water → HCID 68027113, compound

HRID 527928Notes

Reaction equation

HRID 527928 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([N:8]([CH3:31])[C@@H:9]2[CH2:13][CH2:12][N:11]([C:14]3[C:15]4[CH:22]=[CH:21][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:16]=4[N:17]=[CH:18][N:19]=3)[CH2:10]2)=[N:6][CH:7]=1.[O-]CC.[Na+].O>CCO>[CH3:31][N:8]([C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[CH:22]=[CH:21][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:28])([CH3:30])[CH3:29])[C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:10]1)[C:5]1[CH:4]=[N:3][CH:2]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2723922Sodium ethoxideHCID 86692149HCID 86692149, compound

Product 1

HCID 68027113HCID 68027113, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (R)-5-bromo-N-methyl-N-(1-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)pyrazin-2-amine (55 mg, 0.10 mmol) and sodium ethoxide (680 mg, 10 mmol) in EtOH (10.5 mL) was stirred at refluxing temperature for 5 days. It was then treated with water and extracted with EtOAc (2×30 mL). The combined extracts were concentrated and the residue was purified by chromatography on silica gel (PE/EtOAc=1/1). The first compound from the column was collected and confirmed to be (R)-5-ethoxy-N-methyl-N-(1-(7-((2-(trimethylsilyl)ethoxy)-methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)pyrazin-2-amine [MS (m/z), 470 (M+1)+, 21 mg, 41.1% yield) and the later compound from the column was isolated and concentrated to give the title compound (22 mg, 47.8% yield). MS (m/z), 426 (M+1)+

Workup

  1. temperatureat refluxing temperature for 5 days
  2. extractionextracted with EtOAc (2×30 mL)
  3. concentrationThe combined extracts were concentrated
  4. customthe residue was purified by chromatography on silica gel (PE/EtOAc=1/1)
  5. customThe first compound from the column was collected
  6. custom21 mg, 41.1% yield) and the later compound from the column was isolated
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8ffc5ae1c7f44d6f82d517a323f1ba28
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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