Potassium Carbonate → HCID 178429526, compound

HRID 630113Notes

Reaction equation

HRID 630113 reaction equation
Cl.[Cl:2][C:3]1[N:7]([CH3:8])[CH:6]=[N:5][C:4]=1[CH2:9]Cl.[CH3:11][C:12]1[N:17]=[C:16]([SH:18])[N:15]=[C:14]([OH:19])[CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:2][C:3]1[N:7]([CH3:8])[CH:6]=[N:5][C:4]=1[CH2:9][S:18][C:16]1[N:15]=[C:14]([OH:19])[CH:13]=[C:12]([CH3:11])[N:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 668208135-chloro-4-(chloromethyl)-1-methyl-1H-imidazole hydrochlorideHCID 178429541HCID 178429541, compound

Product 1

HCID 178429526HCID 178429526, compoundYield 246.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-chloro-4-(chloromethyl)-1-methyl-1H-imidazole hydrochloride (463 mg, 2.3 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (213 mg, 1.5 mmol), and potassium carbonate (1.1 g, 8.0 mmol) in acetone (15 mL) was stirred at room temperature overnight. The solid material was removed by filtration and washed with 50% acetone/MeOH (2×15 mL). The filtrate was recovered and evaporated. The crude product was purified by flash chromatography (0-10% MeOH/DCM and 0-6% MeOH/DCM), affording 2-{[(5-chloro-1-methyl-1H-imidazol-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (1.0 g, 93% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.17 (s, 3H), 3.53 (s, 3H), 4.25 (s, 2H), 5.97 (s, 1H), 7.70 (s, 1H); M+271. The product was used without further purification.

Workup

  1. customThe solid material was removed by filtration
  2. washwashed with 50% acetone/MeOH (2×15 mL)
  3. customThe filtrate was recovered
  4. customevaporated
  5. customThe crude product was purified by flash chromatography (0-10% MeOH/DCM and 0-6% MeOH/DCM)

Sources & evidence

ORD record
ord-a72ee647e55a458db2434f13407e5371
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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