Water → 6-bromo-8-cyclopentyl-2-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 272424Notes

Reaction equation

HRID 272424 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[CH:3]=1.N[C:22]1C=CC(C(N)=O)=CN=1.O.C(OCC)C>C1(C)C=CC=CC=1.CS(C)=O>[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]([CH3:22])[N:8]=[CH:9][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 95006-AminonicotinamideHCID 114282326-bromo-8-cyclopentyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 101496266-bromo-8-cyclopentyl-2-methyl-8H-pyrido[2,3-d]pyrimidin-7-oneYield 24.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

6-Bromo-8-cyclopentyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (1.09 g, 3.06 mmol) and 6-amino-nicotinamide (2.51 g, 18 mmol) were combined in toluene (8 ml) and heated to 100° C. for 18 hours. The mixture then was diluted with dimethylsulfoxide (8 ml) and heated to 120° C. for 2 hours. The mixture then was poured into water (120 ml) with rapid stirring. Diethyl ether was added and the resulting solid was collected by filtration. This solid was washed with 1:1 warm ethyl acetate/tetrahydrofuran and dried in vacuo to provide 6-bromo-8-cyclopentyl-2-methyl-8H-pyrido[2,3-d]pyrimidin-7-one as a yellow solid (0.233 g, 18%). MS (APCI); M++1: Calc'd, 429.06. Found, 429.1. Analyses for C18H17BrN6O2:

Workup

  1. temperatureheated to 120° C. for 2 hours
  2. filtrationthe resulting solid was collected by filtration
  3. washThis solid was washed with 1:1
  4. temperaturewarm ethyl acetate/tetrahydrofuran
  5. customdried in vacuo

Sources & evidence

ORD record
ord-62c6c094c0704d9ab1b9c19cd236ea8d
Source dataset
uspto-grants-2008_11
Patent number
US07456168B2

Reaction notes

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