Hydrazine → HCID 57593197, compound

HRID 1784467Notes

Reaction equation

HRID 1784467 reaction equation
[CH2:1]([C:8]1[C:13](=[O:14])[N:12]2[CH2:15][CH2:16][CH2:17][CH2:18][C:11]2=[N:10][C:9]=1[CH:19]([N:23]1C(=O)C2C(=CC=CC=2)C1=O)[CH:20]([CH3:22])[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN>C(O)C>[NH2:23][CH:19]([C:9]1[N:10]=[C:11]2[CH2:18][CH2:17][CH2:16][CH2:15][N:12]2[C:13](=[O:14])[C:8]=1[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:20]([CH3:21])[CH3:22]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 57593205HCID 57593205, compound

Product 1

HCID 57593197HCID 57593197, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Step 9 (19), 95 mg (0.22 mmol) was dissolved in 3 ml of dry ethanol then 50 μl (1.6 mmol) of hydrazine was added and the reaction was left to stir at room temperature for 1 h then heated to 40° C. for 2.5 h. The precipitate was removed by filtration and washed with ethyl acetate and the solvent evaporated off resulting in 75 mg of crude 2-(1-amino-2-methylpropyl)-3-benzyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (20). This was purified on a silica column yielding 42 mg (0.13 mmol 63%) as a clear oil.

Workup

  1. waitthe reaction was left
  2. temperaturethen heated to 40° C. for 2.5 h
  3. customThe precipitate was removed by filtration
  4. washwashed with ethyl acetate
  5. customthe solvent evaporated off
  6. customresulting in 75 mg of crude 2-(1-amino-2-methylpropyl)-3-benzyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (20)
  7. customThis was purified on a silica column
  8. customyielding 42 mg (0.13 mmol 63%) as a clear oil

Sources & evidence

ORD record
ord-052f3e5dd9644c4a82306ccb302e5a38
Source dataset
uspto-grants-2009_03
Patent number
US07504405B2

Reaction notes

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