Methyl iodide → HCID 77750436, compound

HRID 1069034Notes

Reaction equation

HRID 1069034 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[CH2:13][N:14]([CH:54]1[CH2:56][CH:55]1[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:15]1[C:16]2[N:27]=[N:26][N:25]([CH:28]3[CH:32]([OH:33])[CH:31]([OH:34])[CH:30]([CH2:35][O:36][Si:37]([C:50]([CH3:53])([CH3:52])[CH3:51])([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH2:29]3)[C:17]=2[N:18]=[C:19]([S:21][CH2:22][CH2:23][CH3:24])[N:20]=1.[CH3:63]I.[Cl-].[NH4+]>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[CH2:13][N:14]([CH:54]1[CH2:56][CH:55]1[C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1)[C:15]1[C:16]2[N:27]=[N:26][N:25]([CH:28]3[CH:32]([OH:33])[CH:31]([O:34][CH3:63])[CH:30]([CH2:35][O:36][Si:37]([C:50]([CH3:52])([CH3:53])[CH3:51])([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[CH2:29]3)[C:17]=2[N:18]=[C:19]([S:21][CH2:22][CH2:23][CH3:24])[N:20]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 77750365HCID 77750365, compound

Product 1

HCID 77750436HCID 77750436, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (65.3 mg) was added to a solution of the diol from step (b) (1.23 g) and methyl iodide (0.13 ml) in DMF (4 ml) and the mixture was stirred for 4 h. Ammonium chloride solution was added and the mixture was extracted with ethyl acetate. The organic extracts were dried, concentrated and purified (SiO2, petrol:acetone 4:1 and petrol:ethyl acetate 2:1 as eluants) to give the subtitle compound (676 mg) as a 1:2.5 mixture with the regioisomeric [1R-[1α,2α,3β,5β(1R*,2S*)]]-3-[7-[N-(2,4-dimethoxyphenylmethyl)-(2-phenylcyclopropyl)amino]]-5-propylthio-3H-1,2,3-triazolo[4,5d]pyrimidin-3-yl]-5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2-methoxycyclopentanol compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic extracts were dried
  3. concentrationconcentrated
  4. custompurified (SiO2, petrol:acetone 4:1 and petrol:ethyl acetate 2:1 as eluants)

Sources & evidence

ORD record
ord-628f7ef851094814b91acf13e53527e8
Source dataset
uspto-grants-2001_06
Patent number
US06251910B1

Reaction notes

Loading…