Acetic Acid → {(1R,2R,4S)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-[(6-{[(1S,2R)-2-methoxy-2,3-dihydro-1H-inden-1-yl]amino}pyrimidin-4-yl)amino]cyclopentyl}methanol

HRID 447624Notes

Reaction equation

HRID 447624 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]([NH:23][C:24]2[CH:29]=[C:28]([NH2:30])[N:27]=[C:26]([C@H]3C4C(=CC=CC=4)C[C@@H]3OC)[N:25]=2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:42][C:43](O)=O.[CH2:46]1[CH2:50][O:49][CH2:48][CH2:47]1>O>[Si:1]([O:8][C@@H:9]1[CH2:10][C@@H:11]([NH:23][C:24]2[CH:29]=[C:28]([NH:30][C@H:46]3[C:47]4[C:10](=[CH:9][CH:13]=[CH:43][CH:42]=4)[CH2:11][C@H:50]3[O:49][CH3:48])[N:27]=[CH:26][N:25]=2)[CH2:12][C@@H:13]1[CH2:14][OH:15])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 66798205N-[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl (dimethyl)silyl]oxy}methyl)cyclopentyl][(1R,2S)-2-methoxy-2,3-dihydro-1H-inden-1-yl]pyrimidine-4,6-diamine

Product 1

HCID 66797967{(1R,2R,4S)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-[(6-{[(1S,2R)-2-methoxy-2,3-dihydro-1H-inden-1-yl]amino}pyrimidin-4-yl)amino]cyclopentyl}methanolYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of N-[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl (dimethyl)silyl]oxy}methyl)cyclopentyl][(1R,2S)-2-methoxy-2,3-dihydro-1H-inden-1-yl]pyrimidine-4,6-diamine (0.188 g, 0.314 mmol) in THF (1.70 mL) and H2O (1.70 mL) was added AcOH (5.08 mL). The solution was stirred overnight then concentrated in vacuo and purified by flash chromatography (0 to 5% MeOH/EtOAc) to obtain the title compound (0.112 g, 74%). LC/MS: Rt=1.46 min, ES+ 485 (Formic Acid).

Workup

  1. concentrationthen concentrated in vacuo
  2. custompurified by flash chromatography (0 to 5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-cd0f1eb5d74840b89e2c75839943a08f
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

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