2-Bromopyrimidine → HCID 54110855, compound

HRID 1369245Notes

Reaction equation

HRID 1369245 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[CH2:15][CH:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:13]3[CH:22]=[CH:23][CH:24]=[CH:25][C:12]=3[CH2:11][C:10]=2[CH:26]=1.C(=O)(O)[O-].[Na+].Br[C:33]1[N:38]=[CH:37][CH:36]=[CH:35][N:34]=1>C(O)C>[N:34]1[CH:35]=[CH:36][CH:37]=[N:38][C:33]=1[NH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[CH2:15][CH:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:13]3[CH:22]=[CH:23][CH:24]=[CH:25][C:12]=3[CH2:11][C:10]=2[CH:26]=1

Participants

5

Reactant 3

HCID 783452-BromopyrimidineHCID 516892Sodium BicarbonateHCID 54488533HCID 54488533, compound

Product 1

HCID 54110855HCID 54110855, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl (±)-10,11-dihydro-3-(3-amino-1-propyloxy)-5H-dibenzo[a,d]cycloheptene-10-acetate (0.4 g, 1 mmole), sodium bicarbonate (0.5 g, 6 mmole), 2-bromopyrimidine (0.34 g, 2 mmole) and ethanol (10 mL) was heated at reflux under argon for 18 hr. The solution was then decanted and concentrated. The residue was purified by chromatography on silica gel (0.2-2% MeOH/CH2Cl2) to give the title compound (0.17 g, 34%) as a pale yellow oil: MS (ES) 432.3 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under argon for 18 hr
  3. customThe solution was then decanted
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (0.2-2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-fc831c37d59c41c29ac9945468fc5e5d
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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