Acetonitrile → HCID 57897819, compound

HRID 1693539Notes

Reaction equation

Br[C:2]1[N:3]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:4]2[N:5]=[C:6]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[N:7]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[C:8](=[O:11])[C:9]=2[N:10]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:41]([NH:43][CH3:44])[CH3:42].C(#N)C>C(Cl)Cl>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([N:7]2[C:8](=[O:11])[C:9]3[N:10]=[C:2]([N:43]([CH2:41][CH3:42])[CH3:44])[N:3]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:4]=3[N:5]=[C:6]2[C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][CH:20]=2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 200 °C

Procedure

8-Bromo-1-(4-chloro-phenyl)-9-phenyl-2-(4-trifluoromethyl-phenyl)-1,9-dihydro-purin-6-one (19.0 mg, 0.0348 mmol), potassium carbonate (400 mg, 2.89 mmol), and ethyl-methyl-amine (172 mg, 2.91 mmol) are mixed in a microwave tube with 1 mL of dry acetonitrile. The tube is then capped and heated to 200° C. for 40 min in a microwave reactor. Then the reaction mixture is diluted with CH2Cl2 and filtered. The filtrate is evaporated and the crude product is purified by column chromatography, yielding 9 mg (49%) of the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.54 (m, 4H), 7.47 (m, 1H), 7.42 (d, 2H), 7.30 (d, 4H), 7.08 (d, 2H), 3.17 (q, 2H), 2.90 (s, 3H), 1.03 (t, 3H). HPLC-MS calculated for C27H21ClF3N5O (M+H+) 524.1. Found: 524.1.

Workup

customThe tube is then capped
filtrationfiltered
customThe filtrate is evaporated
customthe crude product is purified by column chromatography

Sources & evidence

ORD record: ord-fcb4637d20134d7aa6fc575d74e0ebcb
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158634B2

Reaction notes

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