Diisopropylethylamine → HCID 59362943, compound

HRID 1668817Notes

Reaction equation

HRID 1668817 reaction equation
C(N(C(C)C)CC)(C)C.[Cl:10][C:11]1[N:16]=[C:15](Cl)[C:14]2[CH2:18][CH2:19][CH2:20][C:13]=2[N:12]=1.[CH3:21][O:22][C:23]([C:25]1([C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=2)[CH2:28][CH2:27][CH2:26]1)=[O:24]>C(O)C>[CH3:21][O:22][C:23]([C:25]1([C:29]2[CH:30]=[CH:31][C:32]([NH:35][C:15]3[C:14]4[CH2:18][CH2:19][CH2:20][C:13]=4[N:12]=[C:11]([Cl:10])[N:16]=3)=[CH:33][CH:34]=2)[CH2:26][CH2:27][CH2:28]1)=[O:24]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2313312,4-dichloro-5H,6H,7H-cyclopenta(d)pyrimidineHCID 593622601215017-84-7

Product 1

HCID 59362943HCID 59362943, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

Diisopropylethylamine (45.9 mL, 264.55 mmol) was added slowly to a solution of 2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine (10 g, 52.91 mmol) and 1-(4-amino-phenyl)-cyclobutanecarboxylic acid methyl ester (13.015 g, 63.49 mmol) in anhydrous ethanol (100 mL) under stirring at 10° C. Thereafter, the mixture was heated at reflux for 48 hours and then concentrated under reduced pressure. The residue was purified by chromatography (silica gel) to afford the title compound as a light yellow solid (11.7 g, 62% yield).

Workup

  1. temperatureThereafter, the mixture was heated
  2. temperatureat reflux for 48 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography (silica gel)

Sources & evidence

ORD record
ord-43b56519fcbd4382a78790361c36c524
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

Loading…