Hydrochloric Acid → HCID 178429494, compound

HRID 577164Notes

Reaction equation

HRID 577164 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:15]=2[C:16]([F:19])([F:18])[F:17])[N:5]=[C:4]([OH:20])[CH:3]=1.[ClH:21].O1CCOCC1>CO>[ClH:21].[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:15]=2[C:16]([F:19])([F:18])[F:17])[N:5]=[C:4]([OH:20])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178429493HCID 178429493, compound

Product 1

HCID 178429494HCID 178429494, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-methyl-2-({[4-(trifluoromethyl)pyridin-3-yl]methyl}sulfanyl)pyrimidin-4-ol, (150 mg, 498 μmol) was stirred in methanol (20 mL) and a solution of 4 N HCl in dioxane (190 μL, 747 μmol) was added dropwise at 0° C. The mixture was stirred for 15 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-({[4-(trifluoromethyl)pyridin-3-yl]methyl}sulfanyl)pyrimidin-4-ol hydrochloride (147 mg, 88% yield); 1H NMR (400 MHz, DMSO-d6) δ 2.23 (s, 3H), 4.60 (s, 2H), 6.11 (s, 1H), 7.78 (d, J=5.1 Hz, 1H), 8.78 (d, J=5.1 Hz, 1H), 9.04 (s, 1H); LRMS (ES+) m/z 302 (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-e2c64d1e0ba84eb19ee888d2cc09ca00
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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