5-(Piperidin-1-yl)pyridin-2-amine → Pyrido-[2,3-d]-pyrimidin-7-one 49

HRID 1271998Notes

Reaction equation

HRID 1271998 reaction equation
[Br:1][C:2]1[C:14](=[O:15])[N:13]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:5]2[N:6]=[C:7](S(C)=O)[N:8]=[CH:9][C:4]=2[C:3]=1[CH3:21].[N:22]1([C:28]2[CH:29]=[N:30][C:31]([NH2:34])=[CH:32][CH:33]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:14](=[O:15])[N:13]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:5]2[N:6]=[C:7]([NH:34][C:31]3[N:30]=[CH:29][C:28]([N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:33][CH:32]=3)[N:8]=[CH:9][C:4]=2[C:3]=1[CH3:21]

Participants

4

Reactant 2

HCID 112982775-(Piperidin-1-yl)pyridin-2-amineHCID 113721276-bromo-8-cyclopentyl-5-methyl-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 5330292Pyrido-[2,3-d]-pyrimidin-7-one 49Yield 27.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-Bromo-8-cyclopentyl-2-methanesulfinyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (1.0 g, 2.70 mmol) and 3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-6′-ylamine (0.668 g, 3.73 mmol) were heated to reflux in toluene (10 mL) for 16 hours. The reaction mixture was cooled to room temperature and the precipitate that formed was collected by filtration and washed on the funnel with toluene (3×10 mL) to give 6-bromo-8-cyclopentyl-5-methyl-2-(3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-6′-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one as a brown solid (0.358 g, 27.3%). 1H NMR δ (400 MHz, CDCl3) 8.79 (s, 1H), 8.27 (s, 1H), 8.17 (d, J=9.0 Hz, 1H), 8.01 (s, 1H), 7.38 (d, J=6.8 Hz, 1H), 5.98 (m, 1H), 3.1 (m, 4H), 2.60 (s, 3H), 2.30 (m, 2H), 2.11 (m, 2H), 1.88 (m, 2H), 1.57–1.75 (m, 8H).

Workup

  1. customthe precipitate that formed
  2. filtrationwas collected by filtration
  3. washwashed on the funnel with toluene (3×10 mL)

Sources & evidence

ORD record
ord-8b3cf238ce3b4dc2990845a6a434855a
Source dataset
uspto-grants-2007_04
Patent number
US07208489B2

Reaction notes

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