Acetic Anhydride → N-(2-{[(3,5-dichloropyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-yl)acetamide

HRID 577169Notes

Reaction equation

HRID 577169 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:18])[C:7]=1[CH2:8][S:9][C:10]1[N:15]=[C:14]([NH2:16])[CH:13]=[C:12]([CH3:17])[N:11]=1.C([O-])(O)=O.[Na+].[C:24](OC(=O)C)(=[O:26])[CH3:25]>>[Cl:18][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][S:9][C:10]1[N:15]=[C:14]([NH:16][C:24](=[O:26])[CH3:25])[CH:13]=[C:12]([CH3:17])[N:11]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 595893712-{[(3,5-Dichloropyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-amine

Product 1

HCID 59589396N-(2-{[(3,5-dichloropyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-yl)acetamideYield 23%

Procedure

A mixture of 2-{[(3,5-dichloropyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-amine (500 mg, 1.7 mmol) in acetic anhydride (10 mL) was stirred at reflux overnight. After cooling to room temperature, the mixture was neutralized slowly with a saturated solution of NaHCO3 (aq.) until pH 7-8 was reached. The mixture was extracted with ethyl acetate (2×25 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-3% MeOH/CH2Cl2), affording the title compound (136 mg, 23% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.11 (s, 3H), 2.51 (s, 3H), 4.70 (s, 2H), 7.70 (s, 1H), 8.67 (s, 2H), 10.87 (s (br), 1H); M+ 287.

Workup

  1. temperatureat reflux overnight
  2. extractionThe mixture was extracted with ethyl acetate (2×25 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customdried in vacuo
  7. customThe crude product was purified by flash chromatography (0-3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-96187e761f4847f1865fd84ff13e17cd
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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