Diisopropylethylamine → HCID 89422676, compound

HRID 1752441Notes

Reaction equation

HRID 1752441 reaction equation
[N:1]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5][NH:4][CH:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]1.[Cl:18][C:19]1[N:24]=[C:23]([C:25]([O:27][CH3:28])=[O:26])[CH:22]=[C:21](Cl)[N:20]=1.CCN(C(C)C)C(C)C>C(#N)C>[Cl:18][C:19]1[N:20]=[C:21]([N:4]2[CH2:5][CH2:6][N:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:2][CH:3]2[C:7]([O:9][CH3:10])=[O:8])[CH:22]=[C:23]([C:25]([O:27][CH3:28])=[O:26])[N:24]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylateHCID 27568191-tert-Butyl 3-methyl piperazine-1,3-dicarboxylate

Product 1

HCID 89422676HCID 89422676, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-tert-butyl 3-methyl piperazine-1,3-dicarboxylate (5.133 g, 21.01 mmol), methyl 2,6-dichloropyrimidine-4-carboxylate (4.354 g, 21.03 mmol), and iPr2NEt (4.0 mL, 23.0 mmol) in acetonitrile (50 mL) was heated at 50° C. for 4 h. After cooling, the reaction mixture was evaporated in vacuo and the residue chromatographed over silica gel with 20-70% EtOAc in hexanes. The product fractions were evaporated in vacuo to give 1-tert-butyl 3-methyl 4-(2-chloro-6-(methoxycarbonyl)pyrimidin-4-yl)piperazine-1,3-dicarboxylate as a very pale yellow powder (6.626 g, 15.97 mmol, 76% yield). LC/MS: m/z=415.2 [M+H]+.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was evaporated in vacuo
  3. customthe residue chromatographed over silica gel with 20-70% EtOAc in hexanes
  4. customThe product fractions were evaporated in vacuo

Sources & evidence

ORD record
ord-cbff439c31634f9ba8c53503a9d3353c
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

Loading…