Methyl iodide → HCID 11999426, compound

HRID 1668397Notes

Reaction equation

HRID 1668397 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([NH:26][N:27]([CH3:31])[C:28](=[O:30])[CH3:29])=[CH:22][CH:21]=4)[CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[CH3:32]I.[H-].[Na+]>CN(C=O)C.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([N:26]([CH3:32])[N:27]([CH3:31])[C:28](=[O:30])[CH3:29])=[CH:22][CH:21]=4)[CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 59239846HCID 59239846, compound

Product 1

HCID 11999426HCID 11999426, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

N′-[4-[2-[6-(4-Chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl]phenyl]-N-methylacetohydrazide (106 mg) was suspended in DMF (7.0 ml), and methyl iodide (17 μl) and then sodium hydride (60%, 10 mg) were added at 0° C. The obtained mixture was stirred at room temperature for 4.5 hr, and methyl iodide (17 μl) and then sodium hydride (60%, 10 mg) were added at 0° C. The obtained mixture was stirred at room temperature for 24 hr, diluted with chloroform, and washed with water and then saturated brine. The organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=50:1 (volume ratio)) and further washed with ethyl acetate to give the title compound (50.1 mg) as colorless crystals.

Workup

  1. stirringThe obtained mixture was stirred at room temperature for 24 hr
  2. washwashed with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=50:1 (volume ratio))
  6. washfurther washed with ethyl acetate

Sources & evidence

ORD record
ord-d2ede690c64a4142bc2d29cdd16390ea
Source dataset
uspto-grants-2011_08
Patent number
US07989445B2

Reaction notes

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