Acetone → HCID 178429507, compound

HRID 630079Notes

Reaction equation

HRID 630079 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]([CH2:9]O)=[CH:7][N:6]=[CH:5]1)[CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH3:17][C:18]1[N:23]=[C:22]([SH:24])[N:21]=[C:20]([OH:25])[CH:19]=1.CC(C)=O>O=S(Cl)Cl.C(OCC)C>[CH3:17][C:18]1[N:23]=[C:22]([S:24][CH2:9][C:8]2[N:4]([CH:2]([CH3:1])[CH3:3])[CH:5]=[N:6][CH:7]=2)[N:21]=[C:20]([OH:25])[CH:19]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 20568531(1-(propan-2-yl)-1H-imidazol-5-yl)methanolHCID 178429541HCID 178429541, compound

Product 1

HCID 178429507HCID 178429507, compoundYield 40.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 24386Thionyl ChlorideSolvent

Procedure

[1-(propan-2-yl)-1H-imidazol-5-yl]methanol (255 mg, 1.8 mmol) was dissolved in SOCl2 (2 mL) and diethyl ether (10 mL). After 3 hours, the solvents were evaporated. To the solid was added potassium carbonate (414 mg, 3 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (200 mg, 1.4 mmol), and acetone (20 mL). The resulting mixture was stirred at room temperature overnight. Acetone was evaporated, and the crude solid was purified by column chromatography to provide the title compound as a white solid (150 mg, 32% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.51 (m, 6H), 2.27 (s, 3H), 4.53 (m, 1H), 4.92 (s, 2H), 6.01 (br, 1H), 6.99 (s, 1H), 7.83 (s, 1H); M+265.

Workup

  1. customthe solvents were evaporated
  2. customAcetone was evaporated
  3. customthe crude solid was purified by column chromatography

Sources & evidence

ORD record
ord-ee5678ae227b46569945ba5e2604a632
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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