Triethylamine → HCID 54141581, compound

HRID 1458664Notes

Reaction equation

HRID 1458664 reaction equation
O[C:2]1[C:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([CH3:14])[N:5]=[CH:4][N:3]=1.C(N(CC)CC)C.P(Cl)(Cl)([Cl:24])=O.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:24][C:2]1[C:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([CH3:14])[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychloride2×HCID 516892Sodium Bicarbonate2×HCID 178470709HCID 178470709, compound

Product 1

HCID 54141581HCID 54141581, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

30.6 g (0.16 mol) of ethyl (4-hydroxy-6-methylpyrimidin-5-yl)acetate, 17.8 g (0.18 mol) of triethylamine and 263.2 g (1.72 mol) of phosphorus oxychloride were heated at reflux for 4 hours. The excess phosphorus oxychloride was stripped off, the residue was taken up in dichloromethane, and the mixture was added dropwise to 500 ml of sodium bicarbonate solution and neutralized by addition of solid sodium bicarbonate. The organic phase was separated off, dried and concentrated to give 30.4 g (88.5% of theory) of a dark oil which was reacted further without purification.

Workup

  1. temperatureat reflux for 4 hours
  2. customThe organic phase was separated off
  3. customdried
  4. concentrationconcentrated
  5. customto give 30.4 g (88.5% of theory) of a dark oil which
  6. customwas reacted further without purification

Sources & evidence

ORD record
ord-93926fc38c3c447f82a4e852c1e93d48
Source dataset
uspto-grants-1998_12
Patent number
US05852023

Reaction notes

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