Triethylamine → Ethyl N-(4-chloro-2-pyrimidinyl)-N-methylglycinate

HRID 7632

Reaction equation

HRID 7632 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[CH3:9][NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(N(CC)CC)C>O1CCOCC1>[Cl:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:10]([CH3:9])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 95849Glycine, N-methyl-, ethyl ester

Product 1

HCID 12056459Ethyl N-(4-chloro-2-pyrimidinyl)-N-methylglycinate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

30.0 g (0.20 mol) of 2,4-dichloropyrimidine, 30.9 g (0.20 mol) of ethyl N-methylglycinate and 61.0 g (0.60 mol) of triethylamine in 200 ml of dioxane are stirred at 50° C. for 10 min. The mixture is filtered off with suction and the mother liquor is concentrated to half the original volume. A solid crystallizes out, which is filtered off with suction. The mother liquor is concentrated, the residue is stirred with petroleum ether and the product is filtered off.

Workup

  1. filtrationThe mixture is filtered off with suction
  2. concentrationthe mother liquor is concentrated to half the original volume
  3. customA solid crystallizes out, which
  4. filtrationis filtered off with suction
  5. concentrationThe mother liquor is concentrated
  6. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-8cdd1682398d44799c23b12882d311f3
Source dataset
uspto-grants-2006_08
Patent number
US07087616B2

Linked notes

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