1,8-Diazabicyclo(5.4.0)undec-7-ene → 8-ethyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 1666244Notes

Reaction equation

HRID 1666244 reaction equation
C([O:3][C:4](=O)/[CH:5]=[CH:6]/[C:7]1[C:8]([NH:16][CH2:17][CH3:18])=[N:9][C:10]([S:14][CH3:15])=[N:11][C:12]=1[CH3:13])C.N12CCCN=C1CCCCC2>CCN(C(C)C)C(C)C>[CH2:17]([N:16]1[C:8]2[N:9]=[C:10]([S:14][CH3:15])[N:11]=[C:12]([CH3:13])[C:7]=2[CH:6]=[CH:5][C:4]1=[O:3])[CH3:18]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57606958(E)-ethyl-3-(4-(ethylamino)-6-methyl-2-(methylthio)pyrimidin-5-yl)acrylate

Product 1

HCID 576069558-ethyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 77%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of (E)-ethyl-3-(4-(ethylamino)-6-methyl-2-(methylthio)pyrimidin-5-yl)acrylate (16.8 g, 59.8 mmol) in DIPEA was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 18.21 g, 119.6 mmol) at room temperature. Then the reaction mixture was heated to reflux and reacted for 15 h. After evaporation of solvent, the residue was triturated with acetone. The product 8-ethyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (10.77 g, 77% yield) was collected by filtration. 1H NMR (400 MHz, CDCl3): δ 7.78 (d, J=9.6 Hz, 1H), 6.63 (d, J=9.6 Hz, 1H), 4.5 (q, J=7.2 Hz, 2H), 2.67 (s, 3H), 2.62 (s, 3H), 1.33 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureThen the reaction mixture was heated
  2. temperatureto reflux
  3. customreacted for 15 h
  4. customAfter evaporation of solvent
  5. customthe residue was triturated with acetone

Sources & evidence

ORD record
ord-b86b81f2a2bd426b98f5e0fe7faa2bf6
Source dataset
uspto-grants-2011_10
Patent number
US08044062B2

Reaction notes

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