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

HRID 222158Notes

Reaction equation

HRID 222158 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 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 66618085N-[(1R)-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 66618256(1S,2S,4R)-4-{-4-[(1R)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]-pyrimidin-7-yl}-2-(hydroxymethyl)cyclopentanolYield 52.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-[(1R)-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 (70.0 mg, 0.145 mmol) was added to a solution of AcOH (0.742 mL, 13.0 mmol), THF (0.235 mL) and water (0.261 mL). The solution was stirred at rt for 4 days before being concentrated in vacuo. Silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM afforded the title compound (27.6 mg, 52%). LC/MS: Rt=0.94 min, ES+ 365 (FA standard).

Workup

  1. concentrationbefore being concentrated in vacuo
  2. washSilica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-b5f8e7c5e9ce45f4ba90ec2330fb4d2a
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

Loading…