Sodium Carbonate → 2-(4-Trifluoromethyl-phenyl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one

HRID 1022438Notes

Reaction equation

Cl[C:2]1[NH:3][C:4](=[O:11])[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:27][C:26]([F:29])([F:28])[C:23]1[CH:24]=[CH:25][C:20]([C:2]2[NH:3][C:4](=[O:11])[C:5]3[CH:10]=[CH:9][NH:8][C:6]=3[N:7]=2)=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A microwave reaction vial was charged with 2-chloro-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (Intermediate F) (80 mg, 0.32 mmol), 4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (154 mg, 0.56 mmol), tetrakis(triphenylphosphine)palladium(0) (27.3 mg, 0.024 mmol) and a 2M aqueous sodium carbonate solution (0.75 mL) in ethanol (3 mL). The vial was sealed and the reaction was heated in the microwave at 150° C. for 10 min. At this time, the resulting mixture was filtered through a pad of Celite® and concentrated in vacuo. Flash chromatography (30/1 methylene chloride/methanol) afforded 2-(4-trifluoromethyl-phenyl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (5.0 mg, 3.8%) as a white solid. 1HNMR (400 MHz, DMSO-d6) δ ppm 6.50-6.59 (m, 1H) 7.9 (d, 2H) 7.11-7.19 (m, 1H) 8.3 (d, 2H) 12.1 (s, 1H) 12.3 (s, 1H). LC-MS calcd. for C13H9F3N3O [(M+H)+] 280, obsd. 279.9.

Workup

customA microwave reaction
customThe vial was sealed
filtrationAt this time, the resulting mixture was filtered through a pad of Celite®
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1a8abf6f927441819262f96c91b0a164
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722661B2

Reaction notes

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