Methanol → (R)-tert-butyl 2-(4-benzyl-2-methylpiperazin-1-yl)pyrimidine-4-carboxylate

HRID 509290Notes

Reaction equation

HRID 509290 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:5]=[CH:4][N:3]=1.[CH2:15]([N:22]1[CH2:27][CH2:26][NH:25][C@H:24]([CH3:28])[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)C(C)C)(C)C.CO>C(#N)C>[CH2:15]([N:22]1[CH2:27][CH2:26][N:25]([C:2]2[N:7]=[C:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:5]=[CH:4][N:3]=2)[C@H:24]([CH3:28])[CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 6923226(R)-1-Benzyl-3-methylpiperazineHCID 57063961tert-Butyl 2-chloropyrimidine-4-carboxylate

Product 1

HCID 67468035(R)-tert-butyl 2-(4-benzyl-2-methylpiperazin-1-yl)pyrimidine-4-carboxylateYield 94.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Tert-butyl 2-chloropyrimidine-4-carboxylate (4.12 g, 19.2 mmol) and (R)-1-benzyl-3-methylpiperazine (1.83 g, 9.6 mmol) were suspended in acetonitrile (50 ml), followed by addition of N,N-diisopropylethylamine (3.34 ml, 19.2 mmol), and then the resulting liquid was heated at reflux under nitrogen stream for 15 hours. The resulting reaction liquid was concentrated, followed by addition of distilled water (50 ml), and then extracted with MC (100 ml×2). The organic layer was dried over anhydrous sodium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (1% MeOH/MC), to obtain 3.34 g of yellow solid (94%).

Workup

  1. temperaturethe resulting liquid was heated
  2. temperatureat reflux under nitrogen stream for 15 hours
  3. customThe resulting reaction liquid
  4. concentrationwas concentrated
  5. additionfollowed by addition of distilled water (50 ml)
  6. extractionextracted with MC (100 ml×2)
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. filtrationfollowed by filtration and concentration
  9. customthe residue thus obtained

Sources & evidence

ORD record
ord-fc4ff60023314347bf11e05fb4749aa7
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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