(E)-Ethyl 3-(4-(isopropylamino)-6-methyl-2-(methylthio)pyrimidin-5-yl)acrylate → 8-isopropyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 1666262Notes

Reaction equation

HRID 1666262 reaction equation
[CH:1]([NH:4][C:5]1[C:10](/[CH:11]=[CH:12]/[C:13](OCC)=[O:14])=[C:9]([CH3:18])[N:8]=[C:7]([S:19][CH3:20])[N:6]=1)([CH3:3])[CH3:2]>C(O)(=O)C>[CH:1]([N:4]1[C:5]2[N:6]=[C:7]([S:19][CH3:20])[N:8]=[C:9]([CH3:18])[C:10]=2[CH:11]=[CH:12][C:13]1=[O:14])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 57606959(E)-Ethyl 3-(4-(isopropylamino)-6-methyl-2-(methylthio)pyrimidin-5-yl)acrylate

Product 1

HCID 576069628-isopropyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 57%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(E)-Ethyl 3-(4-(isopropylamino)-6-methyl-2-(methylthio)pyrimidin-5-yl)acrylate (2.5 g, 8.46 mmol) was dissolved in acetic acid by gentle warming. Sample was placed in microwave reactor for 6 h at 180° C., 300 W, and 200 PSI. The product was purified by silica gel column chromatography eluting with 20% ethyl acetate/hexane. Desired fractions were combined and reduced into 8-isopropyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one as a yellow powder (1.20 g, 57% yield) which was then dried under heavy vacuum overnight. 1H NMR (400 MHz, CDCl3) δ 7.74 (d, J=9.6, 1H), 6.58 (d, J=9.6, 1H), 5.84 (br s, 1H), 2.65 (s, 3H), 2.63 (s, 3H), 1.63 (d, J=6.8, 6H).

Workup

  1. customThe product was purified by silica gel column chromatography
  2. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-07cc91bf15b8451c9c740aa40f087df1
Source dataset
uspto-grants-2011_10
Patent number
US08044062B2

Reaction notes

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