6-bromo-8-cyclopentyl-5-methyl-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-one → HCID 10128454, compound

HRID 1272017Notes

Reaction equation

HRID 1272017 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].[CH3:22][CH:23]1[O:28][CH:27]([CH3:29])[CH2:26][N:25]([C:30]2[CH:31]=[CH:32][C:33]([NH2:36])=[N:34][CH:35]=2)[CH2:24]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:36][C:33]3[CH:32]=[CH:31][C:30]([N:25]4[CH2:26][CH:27]([CH3:29])[O:28][CH:23]([CH3:22])[CH2:24]4)=[CH:35][N:34]=3)[N:8]=[CH:9][C:4]=2[C:3]=1[CH3:21]

Participants

4

Reactant 2

HCID 113721276-bromo-8-cyclopentyl-5-methyl-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-oneHCID 11469830HCID 11469830, compound

Product 1

HCID 10128454HCID 10128454, compoundYield 27.3%

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 5-(2,6-dimethyl-morpholin-4-yl)-pyridin-2-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-2-[5-(2,6-dimethyl-morpholin-4-yl)-pyridin-2-ylamino]-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one as a brown solid (0.358 g, 27.3%). MS (APCI) Calc'd for M+1: 513.2. Found: 513.1. Anal. Calc'd for C24H29BrN6O2: C, 56.14; H, 5.69; N, 16.37. Found; C, 55.90; H, 5.62; N, 16.10.

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-d8040467524042fbbb34e1c9834df19b
Source dataset
uspto-grants-2007_04
Patent number
US07208489B2

Reaction notes

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