Acetic Acid → ((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methanol

HRID 222203Notes

Reaction equation

HRID 222203 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][C@@H:33]4[C:41]5[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=5)[CH2:35][CH2:34]4)[C:26]=3[CH:25]=[CH:24]2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O.C(O)(=O)C>O1CCCC1>[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][C@@H:33]4[C:41]5[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=5)[CH2:35][CH2:34]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 3

HCID 176Acetic AcidHCID 962WaterHCID 589446667-[(1R,3S,4S)-3-[tert-butyl(dimethyl)silyl]oxy-4-([tert-butyl(dimethyl)silyl]-oxymethyl)cyclopentyl]-N-[(1S)-2,3-dihydro-1H-inden-1-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 58944620((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

7-[(1R,3S,4S)-3-[tert-butyl(dimethyl)silyl]oxy-4-([tert-butyl(dimethyl)silyl]-oxymethyl)cyclopentyl]-N-[(1S)-2,3-dihydro-1H-inden-1-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (1.66 g, 0.00280 mol) was dissolved in a mixture of tetrahydrofuran (6.6 mL), water (6.6 mL, 0.36 mol), and acetic acid (19 mL, 0.34 mol). The solution was then heated to 40° C. overnight. The mixture was then cooled and evaporated, azeotroped with toluene (2×50 mL) and the residue was purified by silica gel chromatography eluting with 0 to 100% ethyl acetate in dichloromethane to yield the product as a white solid, 1.05 g (74%). LC/MS: Rt=1.68 min, ES+ 479 (AA standard).

Workup

  1. temperatureThe mixture was then cooled
  2. customevaporated
  3. customazeotroped with toluene (2×50 mL)
  4. customthe residue was purified by silica gel chromatography
  5. washeluting with 0 to 100% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-cdc6bc64d92e4d788e97c5e1d86ab80e
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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