Hydrochloric Acid → HCID 178429514, compound

HRID 577060Notes

Reaction equation

HRID 577060 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[N:11]=[C:12]([CH3:15])[S:13][CH:14]=2)[N:5]=[C:4]([OH:16])[CH:3]=1.[ClH:17].O1CCOCC1>CO>[ClH:17].[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[N:11]=[C:12]([CH3:15])[S:13][CH:14]=2)[N:5]=[C:4]([OH:16])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178429513HCID 178429513, compound

Product 1

HCID 178429514HCID 178429514, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-methyl-2-{[(2-methyl-1,3-thiazol-4-yl)methyl]sulfanyl}pyrimidin-4-ol (200 mg, 790 μmol) was stirred in methanol (25 mL), and a solution of 4 N HCl in dioxane (300 μL, 1.2 mmol) was added dropwise at 0° C. The mixture was stirred for 30 minutes at room temperature. The solvent was removed by evaporation, and the residue was triturated with diethyl ether and dried in vacuo to afford 6-methyl-2-{[(2-methyl-1,3-thiazol-4-yl)methyl]sulfanyl}pyrimidin-4-ol hydrochloride (230 mg, 100% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.22 (s, 3H), 2.64 (s, 3H), 4.44 (s, 2H), 6.10 (bs, 1H), 7.46 (s, 1H); LRMS (ES+) m/z 254 (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-17a2b7e302ca44c1ba4d427fc34fd25c
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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