Sodium Hydroxide → N-Methyl-N-((3R,4R)-4-methyl-1-(phenylmethyl)-3-piperidinyl)-7H-pyrrolo(2,3-d)pyrimidin-4-amine

HRID 1876742Notes

Reaction equation

[OH-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([CH3:16])[CH:12]([N:17]([CH3:37])[C:18]2[C:19]3[CH:26]=[CH:25][N:24](S(C4C=CC(C)=CC=4)(=O)=O)[C:20]=3[N:21]=[CH:22][N:23]=2)[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O>[CH2:3]([N:10]1[CH2:15][CH2:14][C@@H:13]([CH3:16])[C@@H:12]([N:17]([CH3:37])[C:18]2[C:19]3[CH:26]=[CH:25][NH:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a clean, nitrogen-purged reactor were charged 50% sodium hydroxide solution (210 ml) and (1-benzyl-4-methyl-piperidin-3-yl)-methyl-[7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine (30.0 g, 0.061 mol). The mixture was heated to 95-105° C. for a minimum of 5 hours then cooled to 70-90° C. and water (300 ml) was added. The slurry was cooled to room temperature over a minimum of 1.5 hours and held at room temperature for 1 hour. The solids were isolated by filtration and washed with water (120.0 ml) to obtain 25.2 g of the title compound, water wet.

Workup

customTo a clean, nitrogen-purged reactor
temperaturethen cooled to 70-90° C.
temperatureThe slurry was cooled to room temperature over a minimum of 1.5 hours
customThe solids were isolated by filtration
washwashed with water (120.0 ml)

Sources & evidence

ORD record: ord-85810b4314c44c0ca44d0c48cae06d12
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309716B2

Reaction notes

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