HCID 89616064, compound → HCID 89630067, compound

HRID 882177Notes

Reaction equation

HRID 882177 reaction equation
[OH:1][CH2:2][CH:3]([NH:5][C:6]([C:8]1[C:16]2[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)=[N:14][CH:13]=[N:12][C:11]=2[N:10]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:9]=1)=[O:7])[CH3:4]>ClCCl>[N+:23]([C:19]1[CH:18]=[C:17]([C:15]2[C:16]3[C:8]([C:6]([NH:5][CH:3]([CH3:4])[CH:2]=[O:1])=[O:7])=[CH:9][N:10]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:31])([CH3:33])[CH3:32])[C:11]=3[N:12]=[CH:13][N:14]=2)[CH:22]=[CH:21][CH:20]=1)([O-:25])=[O:24]

Participants

3

Reactant 1

HCID 89616064HCID 89616064, compound

Product 1

HCID 89630067HCID 89630067, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(1-hydroxypropan-2-yl)-4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide (800 mg, 1.70 mmol) in dichloromethane (10 mL), was added DMP (1.20 g, 2.83 mmol). The resulting solution was stirred for 2 hours at room temperature and quenched by addition of saturated aqueous NaHCO3. The resulting solution was extracted with ethyl acetate (×3) and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The reaction was purified by chromatography using silica gel, eluting with 1-50% ethyl acetate/petroleum ether. The product was collected and concentrated in vacuo to afford 4-(3-nitrophenyl)-N-(1-oxopropan-2-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide as a yellow oil. LRMS (ESI) calc'd for C22H28N5O5Si [M+H]+: 470, found 470. 1H NMR (400 MHz, CDCl3) δ 9.53 (s, 1H), 9.12 (s, 1H), 9.09 (s, 1H), 8.57-7.68 (m, 5H), 5.80-5.78 (s, 2H), 4.54-4.51 (m, 1H), 3.66-3.62 (m, 2H), 1.36-1.27 (m, 3H), 1.02-0.98 (m, 2H), 0.02 (s, 9H).

Workup

  1. customquenched by addition of saturated aqueous NaHCO3
  2. extractionThe resulting solution was extracted with ethyl acetate (×3)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe reaction was purified by chromatography
  8. washeluting with 1-50% ethyl acetate/petroleum ether
  9. customThe product was collected
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae8814dd9479472098baa8515d282e24
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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