Hydrochloric Acid → 6-methyl-2-(1,3-thiazol-4-ylmethylsulfanyl)-1H-pyrimidin-4-one;hydrochloride

HRID 577048Notes

Reaction equation

HRID 577048 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[N:11]=[CH:12][S:13][CH:14]=2)[N:5]=[C:4]([OH:15])[CH:3]=1.[ClH:16].O1CCOCC1>CO>[ClH:16].[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[N:11]=[CH:12][S:13][CH:14]=2)[N:5]=[C:4]([OH:15])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178429515HCID 178429515, compound

Product 1

HCID 1784295166-methyl-2-(1,3-thiazol-4-ylmethylsulfanyl)-1H-pyrimidin-4-one;hydrochlorideYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-methyl-2-[(1,3-thiazol-4-ylmethyl)sulfanyl]pyrimidin-4-ol, (247 mg, 1.0 mmol) was stirred in methanol (30 mL), and a solution of 4 N HCl in dioxane (390 μL, 1.5 mmol) was added dropwise at 0° C. The mixture was stirred for 1 hour at room temperature. The solvent was removed by evaporation, and the residue was triturated with diethyl ether and dried in vacuo to afford to 6-methyl-2-[(1,3-thiazol-4-ylmethyl)sulfanyl]pyrimidin-4-ol hydrochloride (260 mg, 92% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.27 (s, 3H), 4.58 (s, 2H), 6.19 (s, 1H), 7.73 (d, J=2.0 Hz, 1H), 9.14 (d, J=2.0 Hz, 1H); LRMS (ES+) m/z 240 (100%, M+1).

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was triturated with diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-96c6775dd631409c983f92003fd69ba4
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

Loading…