Triethylamine → HCID 21086142, compound

HRID 14233

Reaction equation

HRID 14233 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([CH3:12])[N:3]=1.[CH2:13]([NH:16][CH2:17][CH2:18][CH3:19])[CH2:14][CH3:15].C(N(CC)CC)C>C1COCC1>[CH2:13]([N:16]([CH2:17][CH2:18][CH3:19])[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([CH3:12])[N:3]=1)[CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8902DipropylamineHCID 2736835Methyl 2-chloro-6-methylpyrimidine-4-carboxylate

Product 1

HCID 21086142HCID 21086142, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-chloro-6-methylpyrimidine-4-carboxylate (0.411 g, 2.20 mmol), di-n-propylamine (0.668 g, 6.60 mmol), triethylamine (0.267 g, 2.64 mmol), and THF (5 ml) was stirred at room temperature for 55 min and then at reflux for 1.3 h, at which time is was cooled and partitioned between ethyl acetate and a mixture of brine and aq. sodium bicarbonate. The organic layer was dried over magnesium sulfate and concentrated and then chromatographed on silica gel using ethyl acetate-hexane (90/10) to give methyl 2-(dipropylamino)-6-methylpyrimidine-4-carboxylate (0.457 g) as a pale yellow liquid.

Workup

  1. temperatureat reflux for 1.3 h, at which time
  2. temperatureis was cooled
  3. custompartitioned between ethyl acetate
  4. additiona mixture of brine and aq. sodium bicarbonate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customchromatographed on silica gel

Sources & evidence

ORD record
ord-dd6c35d8b0724fd29ccb309244a7cd42
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

Loading…