Hydrochloric Acid → HCID 178429471, compound

HRID 629976Notes

Reaction equation

HRID 629976 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=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[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=2)[N:5]=[C:4]([OH:16])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 1784294706-methyl-2-(pyridin-4-ylmethylsulfanyl)-1H-pyrimidin-4-one

Product 1

HCID 178429471HCID 178429471, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-methyl-2-[(pyridin-4-ylmethyl)sulfanyl]pyrimidin-4-ol (100 mg, 429 μmol) was stirred in methanol (10 mL) and a solution of HCl 4N in dioxane (160 μL, 643 mmol) was added dropwise at 0° C. The mixture was stirred for 30 minutes at room temperature. The solvent was removed, and the residue was washed 3 times with diethyl ether and dried in vacuo to afford to 6-methyl-2-[(pyridin-4-ylmethyl)sulfanyl]pyrimidin-4-ol hydrochloride (109 mg, 94% yield); 1H NMR (400 MHz, MeOd4): δ 2.42 (s, 3H), 4.82 (s, 2H), 6.48 (s, 1H), 8.26 (bs, 2H), 8.82 (bs, 2H); LRMS (ES+) m/z 234 (100%, M+1).

Workup

  1. customThe solvent was removed
  2. washthe residue was washed 3 times with diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-8cb3e2716f3d4eca93a89c09d8e02d65
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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