2-Chloropyrimidine → 3-(2-Methyl-pyrimidin-5-yl)-10-(pyrimidin-2-ylamino)-decanoic acid ethyl ester

HRID 860098Notes

Reaction equation

HRID 860098 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH:6]([C:15]1[CH:16]=[N:17][C:18]([CH3:21])=[N:19][CH:20]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])[CH3:2].Cl[C:24]1[N:29]=[CH:28][CH:27]=[CH:26][N:25]=1.C(N(CC)C(C)C)(C)C>C(O)C>[O-:3][CH2:1][CH3:2].[NH4+:14].[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH:6]([C:15]1[CH:16]=[N:17][C:18]([CH3:21])=[N:19][CH:20]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:24]1[N:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[CH3:2]

Participants

6

Reactant 3

HCID 744042-ChloropyrimidineHCID 81531DiisopropylethylamineHCID 2062248310-Amino-3-(2-methyl-pyrimidin-5-yl)-decanoic acid ethyl ester

Product 2

HCID 206224843-(2-Methyl-pyrimidin-5-yl)-10-(pyrimidin-2-ylamino)-decanoic acid ethyl esterYield 66.5%HCID 22341770NH4OEtYield 1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 24-7 (360 mg, 1.17 mmol), 2-chloropyrimidine (145 mg, 1.26 mmol), and N,N-diisopropylethylamine (456 mg, 3.53 mmol) in ethanol (5 mL) was heated to 65° C. in a sealed tube (4 days). The solvent was removed in vacuo and the residue diluted in aqueous sodium carbonate and extracted with two portions of dichloromethane. The combined organics were washed with brine and dried (Na2SO4). The solvent was removed in vacuo. PCTLC (SiO2, 4 mm, 1% NH4OEt; 10% EtOH; 90% CH2Cl2) afforded 24-8 (150 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue diluted in aqueous sodium carbonate
  3. extractionextracted with two portions of dichloromethane
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-edfcac586d7f487986c14474eadd2a0e
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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