HCID 66618206, compound → HCID 66618151, compound

HRID 222176Notes

Reaction equation

HRID 222176 reaction equation
[Si:1]([O:8][C@@H:9]1[C@H:13]([CH2:14][O:15][Si](C(C)(C)C)(C)C)[CH2:12][C@@H:11]([N:23]2[C:27]3[N:28]=[CH:29][N:30]=[C:31]([NH:32][CH2:33][CH:34]4[CH2:36][CH2:35]4)[C:26]=3[CH:25]=[CH:24]2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C1COCC1.N1C=CC=CC=1.F.N1C=CC=CC=1>[Si:1]([O:8][C@H:9]1[CH2:10][C@H:11]([N:23]2[C:27]3[N:28]=[CH:29][N:30]=[C:31]([NH:32][CH2:33][CH:34]4[CH2:36][CH2:35]4)[C:26]=3[CH:25]=[CH:24]2)[CH2:12][C@H:13]1[CH2:14][OH:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 66618206HCID 66618206, compound

Product 1

HCID 66618151HCID 66618151, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 64774Pyridine, hydrofluoride (1:1)Catalyst2×HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

7-[(1R,3S,4S)-3-{[tert-Butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]-oxy}methyl)cyclopentyl]-N-(cyclopropylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (100. mg, 0.188 mmol) was dissolved in THF (0.900 mL) and pyridine (0.900 mL). Pyridine hydrofluoride (7 drops) was added and the reaction was stirred for 5 h. Additional pyridine hydrofluoride (3 drops) was added and the reaction was stirred for 2 h before being quenched with saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted using EtOAc (3×10 mL), and the combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with a gradient of 0 to 50% EtOAc in hexanes to afford the title compound (47.0 mg, 50%). LC/MS: Rt=1.53 min, ES+ 417 (FA standard).

Workup

  1. stirringthe reaction was stirred for 2 h
  2. custombefore being quenched with saturated aqueous sodium bicarbonate solution
  3. extractionThe aqueous layer was extracted
  4. dry with materialthe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with a gradient of 0 to 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-489c6b8f0441483abdb9c3d2a4379032
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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