Phosphorus oxychloride → 4-(4-Chloro-7H-pyrrolo[2,3-D]pyrimidin-6-YL)benzoic acid ethyl ester

HRID 369861Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:21][C:15]3[N:16]=[CH:17][N:18]=[C:19](O)[C:14]=3[CH:13]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:19]1[C:14]2[CH:13]=[C:12]([C:9]3[CH:10]=[CH:11][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=3)[NH:21][C:15]=2[N:16]=[CH:17][N:18]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178468720HCID 178468720, compound

Product 1

HCID 232826964-(4-Chloro-7H-pyrrolo[2,3-D]pyrimidin-6-YL)benzoic acid ethyl ester

Procedure

Analogously to Step 8.3,1.45 g of 6-(4-ethoxycarbonyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ol in 15 ml of phosphorus oxychloride are heated under a protective gas for 2 hours and worked up, yielding the title compound; m.p.: 250° C. (decomp.): TLC-Rf =0.63 (ethyl acetate/hexane [1:1]); FAB-MS: (M+H)+ =302.

Sources & evidence

ORD record: ord-13a59836a3c846ba9d024c04349f3531
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06140332

Reaction notes

Loading…