Triethylamine → HCID 178470708, compound

HRID 1458663Notes

Reaction equation

HRID 1458663 reaction equation
Cl[C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:13])[N:5]=[CH:4][N:3]=1.[C:14]([C@@H:18]1[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20][CH2:19]1)([CH3:17])([CH3:16])[CH3:15].[CH2:25](N(CC)CC)C>O.C1(C)C=CC=CC=1>[C:14]([C@@H:18]1[CH2:19][CH2:20][C@H:21]([NH:24][C:2]2[C:7]([CH2:8][C:9]([O:11][CH2:12][CH3:25])=[O:10])=[C:6]([CH3:13])[N:5]=[CH:4][N:3]=2)[CH2:22][CH2:23]1)([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10954591Methyl (4-chloro-6-methylpyrimidin-5-yl)acetateHCID 178445676HCID 178445676, compound

Product 1

HCID 178470708HCID 178470708, compound

Reagents, catalysts & solvents 1

HCID 22272177Toluene waterSolvent

Procedure

15.2 g (71 mmol) of methyl (4-chloro-6-methylpyrimidin-5-yl)acetate, 11.0 g (71 mmol) of cis-4-tert-butylcyclohexylamine and 20.2 g (0.2 mol) of triethylamine were heated at 80° to 90° C. for 6 hours without solvent. After cooling, the mixture was taken up in water/toluene and the organic phase was dried and concentrated. In the chromatography on silica gel (petroleum ether/ethyl acetate 1:1, then ethyl acetate/methanol 9:1), 5.3 g of chloropyrimidine starting material were first of all retained and then 10.0 g (27.7% of theory) of product were obtained as a yellow solid.

Workup

  1. temperatureAfter cooling
  2. customthe organic phase was dried
  3. concentrationconcentrated
  4. custom10.0 g (27.7% of theory) of product were obtained as a yellow solid

Sources & evidence

ORD record
ord-59f59c62c84f402caf8a9d7bef42ea7b
Source dataset
uspto-grants-1998_12
Patent number
US05852023

Reaction notes

Loading…