Methyl iodide → (7-(Methylthio)[1,3]thiazolo[5,4-d]pyrimidin-2-yl)methanol

HRID 32589Notes

Reaction equation

HRID 32589 reaction equation
[SH:1][C:2]1[C:3]2[N:10]=[C:9]([CH2:11][OH:12])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.I[CH3:14]>[OH-].[Na+]>[CH3:14][S:1][C:2]1[C:3]2[N:10]=[C:9]([CH2:11][OH:12])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 178519945(7-Mercapto[1,3]thiazolo[5,4-d]pyrimidin-2-yl)methanol2×

Product 1

HCID 17965848(7-(Methylthio)[1,3]thiazolo[5,4-d]pyrimidin-2-yl)methanolYield 53%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of (7-mercapto[1,3]thiazolo[5,4-d]pyrimidin-2-yl)methanol (Intermediate 75) (48.3 g) and iodomethane (16.6 mL) in 2M NaOH (450 mL) was stirred at ambient temperature for 5 hours. The crude product was collected by filtration, suspended in water and acidified by addition of 2N HCl. The flocculant solid was collected by filtration, washed with water (200 mL) and ether (200 mL) and dried under vacuum over phosphorus pentoxide to give the title compound as a pale brown solid (27.5 g, 53%);

Workup

  1. filtrationThe crude product was collected by filtration
  2. additionacidified by addition of 2N HCl
  3. filtrationThe flocculant solid was collected by filtration
  4. washwashed with water (200 mL) and ether (200 mL)
  5. dry with materialdried under vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-03887c52836241e78ca4ac93d53adbe9
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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