Dichloromethane → {3-[5-(4-Methylpiperazin-1-yl)pyrimidin-2-yl]phenyl}methanol

HRID 655337Notes

Reaction equation

HRID 655337 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[N:10][C:11]([C:14]3[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=3)[C:17](OC)=[O:18])=[N:12][CH:13]=2)[CH2:4][CH2:3]1.[H-].C([Al+]CC(C)C)C(C)C.S([O-])([O-])(=O)=O.[Na+].[Na+].ClCCl>C1COCC1>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:13]=[N:12][C:11]([C:14]3[CH:15]=[C:16]([CH2:17][OH:18])[CH:21]=[CH:22][CH:23]=3)=[N:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24436Sodium SulfateHCID 21225700Diisobutylaluminumhydride2×HCID 59484904Methyl 3-[5-(4-methylpiperazin-1-yl)pyrimidin-2-yl]-benzoate

Product 1

HCID 59484860{3-[5-(4-Methylpiperazin-1-yl)pyrimidin-2-yl]phenyl}methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

860 mg (2.75 mmol) of methyl 3-[5-(4-methylpiperazin-1-yl)pyrimidin-2-yl]-benzoate are dissolved in 16 ml of THF, and 13.8 ml (13.8 mmol) of 1 M diisobutylaluminium hydride in THF are added dropwise at room temperature, and the reaction mixture is stirred at room temperature for 1 h. A further 13.8 ml (13.8 mmol) of 1 M diisobutylaluminium hydride in THF are added dropwise, and 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. Dichloromethane is added to the gelatinous mixture, which is then stirred for 30 min and filtered. The filtrate is dried over sodium sulfate and evaporated. Yield: 300 mg, yellow solid. The product is reacted further without further purification; HPLC: 1.68 min (method B); ESI: 285 (M+H).

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 1 h
  2. stirringis then stirred for 30 min
  3. filtrationfiltered
  4. dry with materialThe filtrate is dried over sodium sulfate
  5. customevaporated
  6. customThe product is reacted further without further purification
  7. custom1.68 min (method B)

Sources & evidence

ORD record
ord-f28d846ef1e046fdbcc48c98251753ea
Source dataset
uspto-grants-2011_12
Patent number
US08071593B2

Reaction notes

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