Methanol → 2-[[5-[[(2,3-Difluorophenyl)methyl]thio]-2-methoxythiazolo[4,5-d]pyrimidin-7-yl]amino]-2-methyl-1,3-propanediol

HRID 731529Notes

Reaction equation

Cl[C:2]1[S:3][C:4]2[C:9]([NH:10][C:11]([CH3:16])([CH2:14][OH:15])[CH2:12][OH:13])=[N:8][C:7]([S:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=3[F:26])=[N:6][C:5]=2[N:27]=1.[OH-:28].[K+].O.[CH3:31]O>>[F:26][C:20]1[C:21]([F:25])=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][S:17][C:7]1[N:8]=[C:9]([NH:10][C:11]([CH3:16])([CH2:14][OH:15])[CH2:12][OH:13])[C:4]2[S:3][C:2]([O:28][CH3:31])=[N:27][C:5]=2[N:6]=1

Participants

Reactant 4

HCID 887Methanol

HCID 962Water

HCID 14797Potassium Hydroxide

HCID 690601962-[[2-Chloro-5-[[(2,3-difluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-2-methyl-1,3-propanediol

Product 1

HCID 690604962-[[5-[[(2,3-Difluorophenyl)methyl]thio]-2-methoxythiazolo[4,5-d]pyrimidin-7-yl]amino]-2-methyl-1,3-propanediolYield 90%

Conditions

Temperature: 50 °C

Procedure

The product from step (f) (0.339 g) was suspended in methanol (32 ml). Potasium hydroxide (0.088 g) added and mixture stirred at 50° C. for 20 minutes. Neutralised with 2N HCl and solvents removed in vacuo to give an orange residue. Water added to remove inorganics and the yellow solid was collected by filtration to give 0.3 g of desired product. 90% yield.

Workup

customNeutralised with 2N HCl and solvents removed in vacuo
customto give an orange residue
customto remove inorganics
filtrationthe yellow solid was collected by filtration

Sources & evidence

ORD record: ord-df1d178ec1554d3daf70f6b37933fb07
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585867B2

Reaction notes

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