p-Toluenesulfonic acid → HCID 70817177, compound

HRID 82275Notes

Reaction equation

[N:1]1[C:6]2[N:7]([C:10]3([CH2:13][OH:14])[CH2:12][CH2:11]3)[CH:8]=[CH:9][C:5]=2[CH:4]=[N:3][CH:2]=1.[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1.CC1C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[O:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[O:14][CH2:13][C:10]1([N:7]2[C:6]3[N:1]=[CH:2][N:3]=[CH:4][C:5]=3[CH:9]=[CH:8]2)[CH2:11][CH2:12]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of (1-Pyrrolo[2,3-d]pyrimidin-7-yl-cyclopropyl)-methanol (Preparation 247, 240 mg, 1.27 mmol) in THF (12 mL) was added 3,4-dihydro-2H-pyran (0.46 mL, 5.07 mmol) followed by addition of PTSA (24 mg, 0.13 mmol). The reaction mixture was stirred at 60° C. for 4 hours. The reaction mixture was cooled to room temperature, quenched with saturated aqueous sodium bicarbonate solution (15 mL) and extracted with dichloromethane (3×25 mL). The combined organic layer was washed with brine (10 mL), dried over sodium sulphate and evaporated in vacuo. The crude material was purified by column chromatography on silica gel (gradient of dichloromethane:methanol 100:0 to 98:2) to afford the title compound as a light brown gum in 90% yield, 320 mg.

Workup

temperatureThe reaction mixture was cooled to room temperature
customquenched with saturated aqueous sodium bicarbonate solution (15 mL)
extractionextracted with dichloromethane (3×25 mL)
washThe combined organic layer was washed with brine (10 mL)
dry with materialdried over sodium sulphate
customevaporated in vacuo
customThe crude material was purified by column chromatography on silica gel (gradient of dichloromethane:methanol 100:0 to 98:2)

Sources & evidence

ORD record: ord-5e50202df54a4bfb8303d37e07025412
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846698B2

Reaction notes

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