HCID 14049534, compound → 1-[4-(4-Aminopyrimidin-2-yl)piperazin-1-yl]ethan-1-one

HRID 1241362Notes

Reaction equation

HRID 1241362 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[C:14]([NH2:16])[CH:13]=[C:12](Cl)[N:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>C(O)C>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[N:15]=[C:14]([NH2:16])[CH:13]=[CH:12][N:11]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 14049534HCID 14049534, compound

Product 1

HCID 130944181-[4-(4-Aminopyrimidin-2-yl)piperazin-1-yl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(4-acetylpiperazin-1-yl)-6-chloropyrimidin-4-amine 4-3 (0.90 g, 3.52 mmol) was dissolved in 95% ethanol and then evacuated and back flushed with nitrogen before introducing 10% Pd/C (0.50 g). A hydrogen atmosphere was introduced and this suspension was stirred for 2.5 hours. The catalyst was then filtered off and the filtrate was evaporated to a solid. The solid was purified on a silica column (DCM:MeOH:NH4OH 95:5:0.5) and the product 4-4 was isolated upon evaporation. 1H-NMR(DMSO): 7.75 ppm (d, 1H); 6.44 ppm (s, 2H); 5.74 ppm (d, 1H); 3.66 ppm (m, 2H); 3.59 ppm (m, 2H); 3.45 ppm (m, 4H); 2.03 ppm (s, 3H).

Workup

  1. customevacuated
  2. customback flushed with nitrogen
  3. additionbefore introducing 10% Pd/C (0.50 g)
  4. additionA hydrogen atmosphere was introduced
  5. filtrationThe catalyst was then filtered off
  6. customthe filtrate was evaporated to a solid
  7. customThe solid was purified on a silica column (DCM:MeOH:NH4OH 95:5:0.5)

Sources & evidence

ORD record
ord-f5d9e8c904a0426b9b38faf1889eecb7
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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