4-Toluenesulfonyl chloride → 4-Chloro-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 2068994Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

At about 0° C., sodium hydroxide (2 mol/L in water, 8 mL, 1.20 equiv.) was added to a solution of 4-methylbenzene-1-sulfonyl chloride (2.7 g, 13.9 mmol, 1.10 equiv.) and 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (2 g, 12.8 mmol, 1.00 equiv.) in acetone (20 mL). The resulting solution was stirred at about 20° C. for about 6 hours. The solids were collected by filtration and washed with acetone/water to give the title product as a white solid (4.0 g; yield=97%). 1H NMR (300 MHz, CDCl3) δ: 8.78 (s, 1H), 8.11 (d, J=8.4 Hz, 2H), 7.80 (d, J=4.2 Hz, 1H), 7.34 (d, J=8.4 Hz, 2H), 7.73 (d, J=4.2 Hz, 1H), 2.42 (s, 3H). LC-MS: m/z=308/310 (M+H)+.

Workup

filtrationThe solids were collected by filtration
washwashed with acetone/water

Sources & evidence

ORD record: ord-2295409253d342048e8daebc357196bb
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299084B2

Reaction notes

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