Water → HCID 86711299, compound

HRID 336166Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH2:18][C@H:19]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH:20]=[CH2:21])(=O)=O)=CC=1.Cl.[N:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[C:33]([C:41]2[C:49]3[C:48]([NH2:50])=[N:47][CH:46]=[N:45][C:44]=3[NH:43][CH:42]=2)[CH:32]=1.O>CN(C=O)C>[Si:23]([O:22][C@H:19]([CH:20]=[CH2:21])[CH2:18][N:43]1[C:44]2[N:45]=[CH:46][N:47]=[C:48]([NH2:50])[C:49]=2[C:41]([C:33]2[CH:32]=[N:31][C:40]3[C:35]([CH:34]=2)=[CH:36][CH:37]=[CH:38][CH:39]=3)=[CH:42]1)([C:26]([CH3:27])([CH3:28])[CH3:29])([CH3:24])[CH3:25]

Participants

Conditions

Temperature: 90 °C

Procedure

Potassium carbonate (4.0 g) and (R)-2-((tert-butyldimethylsilyl)oxy)but-3-en-1-yl 4-methylbenzenesulfonate (1.43 g) were added to a solution of 5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine hydrochloride (1.22 g) obtained in Step 4 in DMF (12.2 ml) at room temperature, and the mixture was stirred at 90° C. for 20 hours. After the reaction mixture was cooled, water (49 ml) was added thereto, and the resulting mixture was stirred at room temperature for 3 hours. The resulting precipitate was collected by filtration, washed with water, and dried under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: methanol/ethyl acetate) to obtain the title compound (1.31 g) as a light-yellow solid.

Workup

temperatureAfter the reaction mixture was cooled
stirringthe resulting mixture was stirred at room temperature for 3 hours
filtrationThe resulting precipitate was collected by filtration
washwashed with water
customdried under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (developing solvent: methanol/ethyl acetate)

Sources & evidence

ORD record: ord-be057bf081994c82a1b30415e4963206
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889666B2

Reaction notes

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