Dimethylformamide → 3,4-dihydro-3-[1-(phenylmethyl)-4-piperidinyl]-2(1H)-pyrido[2,3-d]-pyrimidinone

HRID 1699232Notes

Reaction equation

HRID 1699232 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=[CH:4][N:3]=1.CN(C)[CH:25]=[O:26]>>[C:17]1([CH2:16][N:13]2[CH2:12][CH2:11][CH:10]([N:9]3[CH2:8][C:7]4[CH:6]=[CH:5][CH:4]=[N:3][C:2]=4[NH:1][C:25]3=[O:26])[CH2:15][CH2:14]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 18321331HCID 18321331, compound

Product 1

HCID 183214893,4-dihydro-3-[1-(phenylmethyl)-4-piperidinyl]-2(1H)-pyrido[2,3-d]-pyrimidinone

Conditions

Temperature
100 °C

Procedure

A mixture of 4.2 g (0.0142 mol) of 2-amino-3-[[[1-(phenylmethyl)-4-piperidinyl]amino]methyl]-pyridine, 2.4 g (0.0148 mol) of N,N′-carbonyldiimidazole and 50 ml of dimethylformamide was heated to 100° C. for 30 minutes. The still warm mixture was stirred into 300 ml of ice water, the precipitate formed was suction filtered and recrystallised from acetonitrile. After drying in vacuo 4.5 g (98.3% of theory) of colourless crystals of melting point 187° C. were obtained.

Workup

  1. customthe precipitate formed
  2. filtrationfiltered
  3. customrecrystallised from acetonitrile
  4. customAfter drying in vacuo 4.5 g (98.3% of theory) of colourless crystals of melting point 187° C.
  5. customwere obtained

Sources & evidence

ORD record
ord-29c4dc7644c843b5bfd97d09c298f2c1
Source dataset
uspto-grants-2002_02
Patent number
US06344449B1

Reaction notes

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