Methyl iodide → HCID 90403111, compound

HRID 2200655Notes

Reaction equation

HRID 2200655 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][S:18]([NH2:21])(=[O:20])=[O:19])[C:12](=[O:22])[N:11]([CH3:23])[C:10]=3[N:9]=[C:8]2[O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]([F:35])([F:34])[F:33])[CH:26]=2)=[CH:4][CH:3]=1.IC.[C:40](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][S:18]([NH:21][CH3:40])(=[O:20])=[O:19])[C:12](=[O:22])[N:11]([CH3:23])[C:10]=3[N:9]=[C:8]2[O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]([F:34])([F:33])[F:35])[CH:26]=2)=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 90403561HCID 90403561, compound

Product 1

HCID 90403111HCID 90403111, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(4-chlorobenzyl)-3-methyl-2,6-dioxo-8-(3-(trifluoromethoxy)phenoxy)-2,3,6,7-tetrahydro-1H-purin-1-yl)methanesulfonamide (0.1 g, 0.18 mmol, example 18) in DMF (3 mL) was added iodomethane (16 mg, 0.18 mmol) and potassium carbonate (36 mg, 0.26 mmol). The reaction was stirred at room temperature overnight. The mixture was partitioned between ethyl acetate and water. The organic layers were combined, dried over sodium sulfate, filtered and concentrated. The crude product was purified by preparative-HPLC to give 1-(7-(4-chlorobenzyl)-3-methyl-2,6-dioxo-8 (3-(trifluoromethoxy)-phenoxy)-2,3,6,7-tetrahydro-1H-purin-1-yl)-N-methylmethanesulfonamide (23 mg, 22.3% yield) as a white solid. 1H-NMR (DMSO-d6) δ 7.63(t, 1H), 7.50(d, 1H), 7.41-7.46(m, 4H), 7.34-7.37(m, 1H), 7.19-7.23(m, 1H), 5.45(s, 2H), 5.20(s, 2H), 3.31(s, 3H), 2.60(d, 3H). LCMS retention time 3.097 min; LCMS MH+ 574

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by preparative-HPLC

Sources & evidence

ORD record
ord-59734fe0bbb7466388ed786e406575ec
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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