Potassium Hydroxide → HCID 66896551, compound

HRID 2381716Notes

Reaction equation

[OH:1][CH2:2][C@H:3]([NH:5][C:6]1[C:7]2[CH:30]=[CH:29][N:28](S(C3C=CC(C)=CC=3)(=O)=O)[C:8]=2[N:9]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([C:25](=[O:27])[CH3:26])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[N:11]=1)[CH3:4].[OH-].[K+]>CO.O1CCOCC1>[OH:1][CH2:2][C@H:3]([NH:5][C:6]1[C:7]2[CH:30]=[CH:29][NH:28][C:8]=2[N:9]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:20][CH2:21][N:22]([C:25](=[O:27])[CH3:26])[CH2:23][CH2:24]3)=[CH:15][CH:14]=2)[N:11]=1)[CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (R)-1-(4-(4-(4-(1-hydroxypropan-2-ylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (25 mg, 0.044 mmol) in MeOH (1 mL) and dioxane (1 mL), aq. 1N KOH (1.0 mL, 1.0 mmol) was added. After being stirred at 60° C. for 3 h, it was concentrated in vacuo. The residue was acidified with HOAc (1 mL), then was purified by HPLC to give (R)-1-(4-(4-(4-(1-hydroxypropan-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (7 mg), MS 410.5 (M+H); UV 202.6, 267.5, 303.1 nm; and (R)-2-(2-(4-(piperazin-1-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)propan-1-ol (3 mg), MS 368.5 (M+H); UV 229.6, 271.0, 301.9 nm.

Workup

concentrationit was concentrated in vacuo
customwas purified by HPLC

Sources & evidence

ORD record: ord-48ddb2bb315442fb90dff254ef8149bd
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258144B2

Reaction notes

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