Diisopropylethylamine → 2-Amino-4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-6-chloropyrimidine-5-carboxaldehyde

HRID 588748Notes

Reaction equation

HRID 588748 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]=[O:10])=[C:4](Cl)[N:3]=1.CCN(C(C)C)C(C)C.[N:21]1([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>CN(C=O)C>[NH2:1][C:2]1[N:3]=[C:4]([N:24]2[CH2:23][CH2:22][N:21]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25]2)[C:5]([CH:9]=[O:10])=[C:6]([Cl:8])[N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2655462-Amino-4,6-dichloropyrimidine-5-carboxaldehyde

Product 1

HCID 894074512-Amino-4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-6-chloropyrimidine-5-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-amino-4,6-dichloropyrimidine-5-carboxaldehyde (3.84 g, 20 mmol) and DIPEA (5.2 mL, 30 mmol) in DMF was added tert-butyl piperazine-1-carboxylate (3.73 g, 20 mmol) portionwise. The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated and the residue obtained was precipitated with H2O. The precipitate was collected, washed with water and dried in vacuo, to provide the title compound as a white solid in quantitative yield. MS (m/z) 342 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue obtained
  3. customwas precipitated with H2O
  4. customThe precipitate was collected
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-92767fc64e594fd0889bf904dbe89207
Source dataset
uspto-grants-2016_01
Patent number
US09227984B2

Reaction notes

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