8-Cyclopentyl-6-ethyl-2-(methanesulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one → HCID 22329929, compound

HRID 272458Notes

Reaction equation

[CH:1]1([N:6]2[C:11]3[N:12]=[C:13](S(C)(=O)=O)[N:14]=[CH:15][C:10]=3[CH:9]=[C:8]([CH2:20][CH3:21])[C:7]2=[O:22])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:23][C:24]1[N:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][CH:33]([OH:36])[CH2:32][CH2:31]2)=[CH:26][CH:25]=1>C(Cl)Cl>[CH:1]1([N:6]2[C:11]3[N:12]=[C:13]([NH:23][C:24]4[N:29]=[CH:28][C:27]([N:30]5[CH2:35][CH2:34][CH:33]([OH:36])[CH2:32][CH2:31]5)=[CH:26][CH:25]=4)[N:14]=[CH:15][C:10]=3[CH:9]=[C:8]([CH2:20][CH3:21])[C:7]2=[O:22])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 140 °C

Procedure

8-Cyclopentyl-6-ethyl-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one (0.115 g, 0.47 mmol) and 6′-amino-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-4-ol (0.117 g, 0.61 mmol) were combined in dry xylenes and heated at 140° C. under nitrogen overnight. The crude reaction mixture then was allowed to cool and diluted with CH2Cl2. A precipitate was collected by filtration and dried in vacuo to give 8-cyclopentyl-6-ethyl-2-(4-hydroxy-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-6′-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one (15 mg, 7%). MS (APCI); M++1: Calc'd, 435.2. Found 435.2.

Workup

customThe crude reaction mixture
temperatureto cool
filtrationA precipitate was collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-d9a2629439d947b494e7d668a7320897
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456168B2

Reaction notes

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