Ethyl chloroformate → HCID 11555361, compound

HRID 2079577Notes

Reaction equation

HRID 2079577 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]3[N:14]=[C:15]([CH3:26])[N:16]=[C:17]([N:18]4[CH2:23][CH2:22][CH:21]([CH2:24][OH:25])[CH2:20][CH2:19]4)[C:12]=3[C:11]([CH3:27])=[CH:10]2)=[C:4]([CH3:28])[CH:3]=1.[H-].[Na+].Cl[C:32]([O:34][CH2:35][CH3:36])=[O:33]>O1CCCC1>[CH2:35]([O:34][C:32](=[O:33])[O:25][CH2:24][CH:21]1[CH2:22][CH2:23][N:18]([C:17]2[C:12]3[C:11]([CH3:27])=[CH:10][N:9]([C:5]4[C:6]([CH3:8])=[CH:7][C:2]([Br:1])=[CH:3][C:4]=4[CH3:28])[C:13]=3[N:14]=[C:15]([CH3:26])[N:16]=2)[CH2:19][CH2:20]1)[CH3:36]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 104785674-Piperidinemethanol, 1-(7-(4-bromo-2,6-dimethylphenyl)-2,5-dimethyl-7H-pyrrolo(2,3-d)pyrimidin-4-yl)-

Product 1

HCID 11555361HCID 11555361, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

{1-[7-(4-Bromo-2,6-dimethylphenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-4-yl}methanol (1.15 g) synthesized in the similar manner as example 1 in tetrahydrofuran (25 mL) was stirred, then NaH (60% in paraffin, 0.10 g) was added and the mixture was heated at reflux for 3 hours. After cooling to 0° C., ethyl chloroformate (0.28 g) in a small amount of tetrahydrofuran was added and the reaction mixture was allowed to reach room temperature and evaporated. The residue was purified over a silica gel on a glass filter (eluent: CH2Cl2/CH3CN=95:5 then 90:10) to give the title product (366 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 hours
  3. customto reach room temperature
  4. customevaporated
  5. customThe residue was purified over a silica gel on a glass
  6. filtrationfilter (eluent

Sources & evidence

ORD record
ord-b04c9f0a6ad04683987abc7df315c32d
Source dataset
uspto-grants-2011_04
Patent number
US07932259B2

Reaction notes

Loading…