Methyl iodide → (7-(Methylthio)[1,3]thiazolo[5,4-d]pyrimidin-2-yl)methanol
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]=1Participants
4
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
- filtrationThe crude product was collected by filtration
- additionacidified by addition of 2N HCl
- filtrationThe flocculant solid was collected by filtration
- washwashed with water (200 mL) and ether (200 mL)
- 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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