Triethylamine → HCID 59655975, compound

HRID 2054610Notes

Reaction equation

HRID 2054610 reaction equation
[CH2:1]([C:8]1[N:13]=[C:12](Cl)[CH: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:23])[CH2:20][CH2:21][NH2:22].C(N(CC)CC)C>CN(C=O)C.O>[CH3:17][O:18][C:19](=[O:23])[CH2:20][CH2:21][NH:22][C:12]1[CH:11]=[C:10]([Cl:15])[N:9]=[C:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[N:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 27752592-benzyl-4,6-dichloropyrimidine

Product 1

HCID 59655975HCID 59655975, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.503 g (2.1 mmole) of 2-benzyl-4,6-dichloro-pyrimidine was dissolved in 10 mls of DMF. To this solution was added 0.340 g of 3-amino-propionic acid methyl ester HCl. Next 0.6 mls of triethyl amine 94.3 mmoles) was added dropwise and the reaction stirred at room temperature for 12 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. 3-(2-benzyl-6-chloro-pyrimidin-4-ylamino)-propionic acid methyl ester (0.531 g, 79%) 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-ce4ae4f33d914183aeb4895fd62fba10
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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