Dichloromethane → HCID 59484849, compound

HRID 2088410Notes

Reaction equation

HRID 2088410 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[N:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[CH:13][N:12]=2)[CH:8]=[CH:9][CH:10]=1)=O.[H-].C([Al+]CC(C)C)C(C)C.S([O-])([O-])(=O)=O.[Na+].[Na+].ClCCl>C1COCC1.CO>[OH:2][CH2:3][C:5]1[CH:6]=[C:7]([C:11]2[N:16]=[CH:15][C:14]([N:17]3[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22]3)=[CH:13][N:12]=2)[CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 24436Sodium SulfateHCID 21225700DiisobutylaluminumhydrideHCID 59484919HCID 59484919, compound

Product 1

HCID 59484849HCID 59484849, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

862 mg (2.16 mmol) of tert-butyl 4-[2-(3-methoxycarbonylphenyl)pyrimidin-5-yl]piperazine-1-carboxylate are dissolved in 15 ml of THF, and 10.8 ml (10.8 mmol) of 1 M diisobutylaluminium hydride in THF are added at room temperature. The reaction mixture is stirred at room temperature for 1 h. 3 ml of saturated sodium sulfate solution are added to the reaction mixture with ice-cooling. 30 ml of dichloromethane and 5 ml of methanol are added to the gelatinous mixture, which is then stirred for 10 min and filtered off through kieselguhr with suction. The filtrate is dried over sodium sulfate and evaporated. The residue is dissolved in dichloromethane, filtered, and the filtrate is evaporated. The product is reacted further without further purification; yield:

Workup

  1. temperaturecooling
  2. stirringis then stirred for 10 min
  3. filtrationfiltered off through kieselguhr with suction
  4. dry with materialThe filtrate is dried over sodium sulfate
  5. customevaporated
  6. dissolutionThe residue is dissolved in dichloromethane
  7. filtrationfiltered
  8. customthe filtrate is evaporated
  9. customThe product is reacted further without further purification

Sources & evidence

ORD record
ord-cd455fa02ff14ac8a720da51e6e661fa
Source dataset
uspto-grants-2013_05
Patent number
US08435986B2

Reaction notes

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