Acetic Acid → (1S,2S,4R)-4-(4-((S)-2,3-dihydro-1H-inden-1-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)cyclopentanol

HRID 552724Notes

Reaction equation

HRID 552724 reaction equation
[C@@H:1]1([NH:10][C:11]2[C:12]3[CH:19]=[CH:18][N:17]([C@H:20]4[CH2:36][C@@H:23]5[O:24]C(C6C=CC(OC)=CC=6)[O:26][CH2:27][C@@H:22]5[CH2:21]4)[C:13]=3[N:14]=[CH:15][N:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.CC(O)=O>C1COCC1.O>[C@@H:1]1([NH:10][C:11]2[C:12]3[CH:19]=[CH:18][N:17]([C@H:20]4[CH2:36][C@H:23]([OH:24])[C@H:22]([CH2:27][OH:26])[CH2:21]4)[C:13]=3[N:14]=[CH:15][N:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 66618654N-((S)-2,3-dihydro-1H-inden-1-yl)-7-((4aS,6R,7aS)-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-6-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 58944696(1S,2S,4R)-4-(4-((S)-2,3-dihydro-1H-inden-1-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)cyclopentanolYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-[(1S)-2,3-dihydro-1H-inden-1-yl]-7-[(4aS,6R,7aS)-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (3.00 g, 5.90 mmol) in THF (11.6 mL), water (11.6 mL) and AcOH (34.9 mL, 614 mmol) was stirred at room temperature under an atmosphere of argon for 60 hours. The mixture was concentrated and the residue was purified via flash chromatography (0 to 10% MeOH/DCM) to afford the title compound (2.10 g, 98%).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified via flash chromatography (0 to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-15d43d58903945fa9e3277351f129d75
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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