Methyl iodide → HCID 178481615, compound

HRID 2074207Notes

Reaction equation

HRID 2074207 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([N:11]2[C:15]3[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:34])[N:6]2[C@H:21]1[CH2:26][CH2:25][C@H:24]([O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[CH2:23][CH2:22]1.[CH3:35]CN(P1(N(C)CCCN1)=NC(C)(C)C)CC.IC>CC#N>[Cl:1][C:2]1[N:10]=[C:9]([N:11]2[C:15]3[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)[N:8]=[C:7]2[C:3]=1[N:4]([CH3:35])[C:5](=[O:34])[N:6]2[C@H:21]1[CH2:26][CH2:25][C@H:24]([O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 199900182-tert-butylimino-N,N-diethyl-1-methyl-1,3,2lambda5-diazaphosphinan-2-amineHCID 178518645HCID 178518645, compound

Product 1

HCID 178481615HCID 178481615, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-chloro-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-9-(trans-4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl)-7H-purin-8(9H)-one (0.06 mmol) in anhydrous CH3CN (10 mL) were added BEMP on polystyrene (loading 2.2 mmol/g, 4 equiv.) and iodomethane (primary alkyl iodide/benzyl iodide or bromide to be used for alkylation) (6 equiv.) with stirring at room temperature. After 1 h, LCMS showed reaction to be complete. The reaction mixture was filtered under vacuum, the resin washed with CH3CN and methanol, and the combined filtrate and washings were concentrated in vacuo to give the desired product as a pale yellow solid, which was used in the next step without further purification. MS (EI) m/z 501.2 (MH)+.

Workup

  1. customreaction
  2. filtrationThe reaction mixture was filtered under vacuum
  3. washthe resin washed with CH3CN and methanol
  4. concentrationthe combined filtrate and washings were concentrated in vacuo

Sources & evidence

ORD record
ord-2965443708684dd9a6f5f1b48df3148d
Source dataset
uspto-grants-2011_04
Patent number
US07919490B2

Reaction notes

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