Acetic Anhydride → HCID 57565624, compound

HRID 1727028Notes

Reaction equation

HRID 1727028 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]([CH2:17][C:18]3[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:25])[C:15]3[C:14](=[O:26])[N:13]([CH3:27])[C:12](=[O:28])[N:11]([CH3:29])[C:10]=3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:30](OC(=O)C)(=[O:32])[CH3:31]>C(Cl)Cl>[Cl:25][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([F:24])[C:18]=1[CH2:17][N:16]1[C:15]2[C:14](=[O:26])[N:13]([CH3:27])[C:12](=[O:28])[N:11]([CH3:29])[C:10]=2[N:9]=[C:8]1[C:4]1[CH:3]=[C:2]([NH:1][C:30](=[O:32])[CH3:31])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 57565688HCID 57565688, compound

Product 1

HCID 57565624HCID 57565624, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 8-(3-aminophenyl)-7-(2-chloro-6-fluorobenzyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione (25 mg, 0.06 mmol) in 255 μL CH2Cl2 was treated with acetic anhydride (6.6 μL, 0.07 mmol). The reaction was stirred for 1.5 hr and then blown dry under nitrogen. The crude product was purified by preparative thin layer chromatography (silica gel, 1 mm plate, EM Science 20×20 cm silica gel 60 F264) eluting with EtOAc:hexane (3:1) to give 4 mg (15% yield) of the title compound as a clear oil: 1H NMR (CDCl3, 400 MHz) 7.67-7.61 (m, 2H), 7.36-7.26 (m, 2H), 7.21-7.15 (m, 1H), 7.13-7.01 (m, 2H), 6.84-6.75 (m, 1H), 5.86 (s, 2H), 3.62 (s, 3H), 3.38 (s, 3H), 2.97 (s, 3H); MS (ESP+) m/e 456 (MH+); TLC (EtOAc:hexanes/3:1) Rf=0.11.

Workup

  1. customblown dry under nitrogen
  2. customThe crude product was purified by preparative thin layer chromatography (silica gel, 1 mm plate, EM Science 20×20 cm silica gel 60 F264)
  3. washeluting with EtOAc:hexane (3:1)

Sources & evidence

ORD record
ord-bcb19b52c5954b848c3412a293cc4c36
Source dataset
uspto-grants-2009_02
Patent number
US07495004B2

Reaction notes

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