Methyl iodide → 2-(6-Fluoro-1H-benzo[d]imidazol-1-yl)-9-((R)-8-fluorochroman-4-yl)-8-(methylthio)-8,9-dihydro-7H-purine

HRID 605874Notes

Reaction equation

HRID 605874 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[N:18]=[C:17]4[C:13]([NH:14][C:15](=[S:30])[N:16]4[C@H:19]4[C:28]5[C:23](=[C:24]([F:29])[CH:25]=[CH:26][CH:27]=5)[O:22][CH2:21][CH2:20]4)=[CH:12][N:11]=3)[C:6]=2[CH:31]=1.[CH3:32]CN(P1(N(C)CCCN1)=NC(C)(C)C)CC.IC>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[N:18]=[C:17]4[C:13]([NH:14][CH:15]([S:30][CH3:32])[N:16]4[C@H:19]4[C:28]5[C:23](=[C:24]([F:29])[CH:25]=[CH:26][CH:27]=5)[O:22][CH2:21][CH2:20]4)=[CH:12][N:11]=3)[C:6]=2[CH:31]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 199900182-tert-butylimino-N,N-diethyl-1-methyl-1,3,2lambda5-diazaphosphinan-2-amineHCID 597048822-(6-Fluoro-1H-benzo[d]imidazol-1-yl)-9-((R)-8-fluorochroman-4-yl)-7H-purine-8(9H)-thione

Product 1

HCID 597048852-(6-Fluoro-1H-benzo[d]imidazol-1-yl)-9-((R)-8-fluorochroman-4-yl)-8-(methylthio)-8,9-dihydro-7H-purineYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(6-Fluoro-1H-benzo[d]imidazol-1-yl)-9-((R)-8-fluorochroman-4-yl)-7H-purine-8(9H)-thione (4 mg, 0.009 mmol) was dissolved in 1 mL anhydrous acetonitrile, add 25 mg (0.054 mmol) 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine on polystyrene (Fluka), then 3 microliter iodomethane. The mixture was stirred at room temperature for 30 minutes. After concentration in vacuo, the residue was purified by silica gel column chromatography eluting with 2% MeOH in DCM and EtOAc to yield 2.1 mg (52%) the titled compound as a pale yellow solid.

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe residue was purified by silica gel column chromatography
  3. washeluting with 2% MeOH in DCM and EtOAc

Sources & evidence

ORD record
ord-b16162f1354e4a1bac841e633503e87c
Source dataset
uspto-grants-2011_03
Patent number
US07915268B2

Reaction notes

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