Hydrochloric Acid → HCID 178429509, compound

HRID 630088Notes

Reaction equation

HRID 630088 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[N:14]([CH3:15])[CH:13]=[N: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[N:14]([CH3:15])[CH:13]=[N:12][CH:11]=2)[N:5]=[C:4]([OH:16])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178429508HCID 178429508, compound

Product 1

HCID 178429509HCID 178429509, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-methyl-2-{[(1-methyl-1H-imidazol-5-yl)methyl]sulfanyl}pyrimidin-4-ol, (252 mg, 1.1 mmol) was stirred in methanol (30 mL), and a solution of 4N HCl in dioxane (400 μL, 1.6 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-methyl-1H-imidazol-5-yl)methyl]sulfanyl}pyrimidin-4-ol hydrochloride (281 mg, 96% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.24 (s, 3H), 3.88 (s, 3H), 4.50 (s, 2H), 6.15 (bs, 1H), 7.65 (s, 1H), 9.09 (s, 1H); LRMS (ES+) m/z 237 (70%, 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-1422d880420c4f22815c0d1a98379680
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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