6-bromo-8-cyclopentyl-5-methyl-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-one → 2-{5-[Bis-(2-methoxy-ethyl)-amino]-pyridin-2-ylamino}-6-bromo-8-cyclopentyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 272461Notes

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][O:23][CH2:24][CH2:25][N:26]([CH2:34][CH2:35][O:36][CH3:37])[C:27]1[CH:28]=[CH:29][C:30]([NH2:33])=[N:31][CH:32]=1>C1(C)C=CC=CC=1>[CH3:37][O:36][CH2:35][CH2:34][N:26]([CH2:25][CH2:24][O:23][CH3:22])[C:27]1[CH:28]=[CH:29][C:30]([NH:33][C:7]2[N:8]=[CH:9][C:4]3[C:3]([CH3:21])=[C:2]([Br:1])[C:14](=[O:15])[N:13]([CH:16]4[CH2:20][CH2:19][CH2:18][CH2:17]4)[C:5]=3[N:6]=2)=[N:31][CH:32]=1

Participants

Conditions

Temperature: 110 °C

Procedure

6-Bromo-8-cyclopentyl-2-methanesulfinyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (0.4 g, 1.08 mmol) and N5,N5-Bis-(2-methoxy-ethyl)-pyridine-2,5-diamine (0.5 g, 2.2 mmol) were combined in toluene (3.5 mL) and heated to 110° C. After 5 h the reaction mixture was allowed to cool and the crude product was directly chromatographed on silica gel eluting with a gradient of 25% to 100% ethyl acetate in hexanes to provide 2-{5-[bis-(2-methoxy-ethyl)-amino]-pyridin-2-ylamino}-6-bromo-8-cyclopentyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (0.49 g, 85%) as an orange gum. mp 94-95° C. MS (APCI); M++1: Calc'd, 530.2. Found 530.1. Anal. Calc'd for C24H32N6O3Br10.13H2O: C, 54.00; H, 5.90; N, 15.74. Found; C, 53.61; H, 5.68; N, 15.60.

Workup

temperatureto cool
customthe crude product was directly chromatographed on silica gel eluting with a gradient of 25% to 100% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-7d30953661c947f9b787ed72ae67de83
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456168B2

Reaction notes

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