Hydrochloric Acid → 6-Chloro-N4-{3-fluoro-4-[(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)amino]phenyl}pyrimidine-2,4-diamine

HRID 2240265Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[NH:16][CH:17]=[C:18]([CH3:19])[C:11]=12.[Cl:20][C:21]1[CH:26]=[C:25](Cl)[N:24]=[C:23]([NH2:28])[N:22]=1.Cl.[OH-].[Na+]>O>[Cl:20][C:21]1[N:22]=[C:23]([NH2:28])[N:24]=[C:25]([NH:8][C:6]2[CH:5]=[CH:4][C:3]([NH:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]4[NH:16][CH:17]=[C:18]([CH3:19])[C:11]=34)=[C:2]([F:1])[CH:7]=2)[CH:26]=1

Participants

Conditions

Temperature: 100 °C

Procedure

19 mg (70 μmol) of 2-fluoro-N1-(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)benzene-1,4-diamine and 17 mg (10 μmol) of 4,6-dichloropyrimidine-2-amine are suspended in 3.5 ml of water. 100 μI of 1 M hydrochloric acid are added, and the mixture is heated at 100° C. overnight. Using 1N aqueous sodium hydroxide solution, the suspension is then adjusted to pH 10, resulting in the precipitation of crystals. The solid is filtered off and washed with water. The crude product is purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol (7M ammonia) 100:1 to 10:1).

Workup

customresulting in the precipitation of crystals
filtrationThe solid is filtered off
washwashed with water
customThe crude product is purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol (7M ammonia) 100:1 to 10:1)

Sources & evidence

ORD record: ord-f7c089c08a524628aa0ffd8d177f9a06
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723347B2

Reaction notes

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