Methyl iodide → HCID 86617564, compound

HRID 2234509Notes

Reaction equation

HRID 2234509 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:6][C:7](=[O:23])[C:8]3([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:9][N:10]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[C:11]=2[N:12]=1.[CH3:24]I.[H-].[Na+]>CN(C)C(=O)C.O.C(OCC)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:6]([CH3:24])[C:7](=[O:23])[C:8]3([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)[CH2:9][N:10]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)[C:11]=2[N:12]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86761104HCID 86761104, compound2×

Product 1

HCID 86617564HCID 86617564, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 31374DimethylacetamideSolvent

Procedure

2′-chloro-9′-cyclopentyl-8′,9′-dihydrospiro[cyclohexane-1,7′-pyrimido[5,4-b][1,4]diazepin]-6′(5′H)-one (Intermediate 256; 300 mg, 0.94 mmol) was dissolved in N,N-dimethylacetamide (10 mL) and methyl iodide (65 mL, 1.03 mmol) added followed by sodium hydride (41 mg of a 60% dispersion in mineral oil, 1.00 mmol). The reaction mixture was stirred for 30 minutes. A drop of water added was added and then the reaction mixture was diluted with water and extracted with ethyl acetate (×2). The combined organic extracts were dried (MgSO4) and concentrated and the residue purified by column chromatography (1% MeOH/DCM) to give a sticky white solid (Note 4) that was suspended in diethyl ether and filtered off to yield the title compound as a white crystalline solid (242 mg, 77%).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate (×2)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. customthe residue purified by column chromatography (1% MeOH/DCM)
  6. customto give a sticky white solid (Note 4) that
  7. filtrationfiltered off

Sources & evidence

ORD record
ord-98fddeef692441529798dfd3c09ef785
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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