Triethylamine → (6-Benzyl-2-chloro-pyrimidin-4-ylamino)-acetic acid methyl ester

HRID 2054609Notes

Reaction equation

HRID 2054609 reaction equation
[CH2:1]([C:8]1[CH:13]=[C:12](Cl)[N:11]=[C:10]([Cl:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:17][O:18][C:19](=[O:22])[CH2:20][NH2:21].C(N(CC)CC)C>CN(C=O)C.O>[CH3:17][O:18][C:19](=[O:22])[CH2:20][NH:21][C:12]1[CH:13]=[C:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:9]=[C:10]([Cl:15])[N:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 462230714-Benzyl-2,6-dichloropyrimidine

Product 1

HCID 86010072(6-Benzyl-2-chloro-pyrimidin-4-ylamino)-acetic acid methyl esterYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

1.87 g (7.8 mmole) of 4-benzyl-2,6-dichloro-pyrimidine was dissolved in 15 mls of DMF. To this solution was added 1.08 g of glycine methyl ester HCl. Next 3.0 mls of triethyl amine was added dropwise and the reaction stirred was then heated to 70° C. for 3 hours. The reaction was diluted with 10 mls of H2O and extracted with two portions of EtOAc. The combined organic layers were washed with two portions of saturated NaCl solution, dried over MgSO4, filter and evaporated under reduced pressure to yield a crude oil. This material was chromatographed on silica gel with 10% Ethyl Acetate-90% Heptane as the eluent. (6-Benzyl-2-chloro-pyrimidin-4-ylamino)-acetic acid methyl ester (0.354 g, 20%) was isolated a clear oil.

Workup

  1. extractionextracted with two portions of EtOAc
  2. washThe combined organic layers were washed with two portions of saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfilter
  5. customevaporated under reduced pressure
  6. customto yield a crude oil
  7. customThis material was chromatographed on silica gel with 10% Ethyl Acetate-90% Heptane as the eluent

Sources & evidence

ORD record
ord-eda7d3f892cd4b5084ab06bdd1621cbe
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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