Dimethylformamide → 4-Methyl-4-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanenitrile

HRID 1501398Notes

Reaction equation

CS(O[CH2:6][CH2:7][C:8]([CH3:24])([N:10]1[CH:14]=[C:13]([C:15]2[C:16]3[CH:23]=[CH:22][NH:21][C:17]=3[N:18]=[CH:19][N:20]=2)[CH:12]=[N:11]1)[CH3:9])(=O)=O.[CH3:25][N:26](C=O)C.[C-]#N.[Na+]>O>[CH3:9][C:8]([N:10]1[CH:14]=[C:13]([C:15]2[C:16]3[CH:23]=[CH:22][NH:21][C:17]=3[N:18]=[CH:19][N:20]=2)[CH:12]=[N:11]1)([CH3:24])[CH2:7][CH2:6][C:25]#[N:26]

Participants

Conditions

Temperature: 125 °C

Procedure

3-methyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butyl methanesulfonate (2.97 g, 8.50 mmol), DMF (120 mL) and sodium cyanide (6.21 g, 0.127 mol) were distributed evenly into six 20 mL microwavable vessels, each of which was heated in the microwave reactor for 4000 seconds at 125° C. The contents of the vials were combined and were diluted with 400 mL water and extracted with five 150 mL portions of ethyl acetate. The combined extracts were dried over sodium sulfate, and the solvent was removed in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (1.40 g, 59%).

Workup

extractionextracted with five 150 mL portions of ethyl acetate
dry with materialThe combined extracts were dried over sodium sulfate
customthe solvent was removed in vacuo
customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record: ord-3dbf858f213a409f9ac8a4f343354ea4
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206187B2

Reaction notes

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