Potassium Carbonate → HCID 980944, compound

HRID 1727019Notes

Reaction equation

HRID 1727019 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[C:8]([Br:11])[NH:7][C:6]=2[C:5](=[O:12])[NH:4][C:3]1=[O:13].C([O-])([O-])=O.[K+].[K+].[Cl:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:22]=1[CH2:23]Br>CN(C=O)C>[Br:11][C:8]1[N:7]([CH2:23][C:22]2[C:25]([F:29])=[CH:26][CH:27]=[CH:28][C:21]=2[Cl:20])[C:6]2[C:5](=[O:12])[NH:4][C:3](=[O:13])[N:2]([CH3:1])[C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15487978-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dioneHCID 27736252-Chloro-6-fluorobenzyl bromide

Product 1

HCID 980944HCID 980944, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3-methyl-8-bromoxanthine (1.5 g, 6.1 mmol, Klein, J. P. PCT Int. Appl. WO 0061583, 2000) and K2CO3 (0.84 g, 6.1 mmol) in 6 mL DMF was treated with 2-chloro-6-fluorobenzyl bromide. The reaction mixture was heated to 60° C. for 2 hr, cooled, and poured onto ice water. The solid precipitate was filtered and dried to yield 1.8 g (76% yield) of a white solid: 1H NMR (DMSO, 400 MHz) 7.43-7.36 (m, 1H), 7.34-7.30 (m, 1H), 7.22-7.15 (m, 1H), 5.67 (s, 2H), 3.29 (s, 3H); MS (AP+) m/e 389 (MH+).

Workup

  1. temperaturecooled
  2. additionpoured onto ice water
  3. filtrationThe solid precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-0c8deb9d112440bf9a4735bb72a0582c
Source dataset
uspto-grants-2009_02
Patent number
US07495004B2

Reaction notes

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