Toluene → 8-Cyclopentyl-6-(1-ethoxy-vinyl)-5-methyl-2-(3,4,5,6-tetrahydro-2H-[1,3']bipyridinyl-6'-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 272494

Reaction equation

HRID 272494 reaction equation
Br[C:2]1[C:24](=[O:25])[N:23]([CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[C:5]2[N:6]=[C:7]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:22]COCC4)=[CH:13][N:12]=3)[N:8]=[CH:9][C:4]=2[C:3]=1[CH3:31].C([Sn](CCCC)(CCCC)[C:37]([O:39][CH2:40][CH3:41])=[CH2:38])CCC.[C:50]1(C)[CH:55]=CC=[CH:52][CH:51]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:26]1([N:23]2[C:5]3[N:6]=[C:7]([NH:10][C:11]4[N:12]=[CH:13][C:14]([N:17]5[CH2:22][CH2:52][CH2:51][CH2:50][CH2:55]5)=[CH:15][CH:16]=4)[N:8]=[CH:9][C:4]=3[C:3]([CH3:31])=[C:2]([C:37]([O:39][CH2:40][CH3:41])=[CH2:38])[C:24]2=[O:25])[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 53302946-Bromo-8-cyclopentyl-5-methyl-2-(5-morpholin-4-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 101279068-Cyclopentyl-6-(1-ethoxy-vinyl)-5-methyl-2-(3,4,5,6-tetrahydro-2H-[1,3']bipyridinyl-6'-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-oneYield 59.2%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

6-Bromo-8-cyclopentyl-5-methyl-2-(5-morpholin-4-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one (0.310 g, 0.641 mmol), tetrakis(triphenylphosphine)palladium (0.089 g, 0.077 mmol) and tributyl-(1-ethoxy-vinyl)-stannane (0.361 g, 1.0 mmol) were dissolved in toluene (3 mL) and slowly brought to reflux for 2 hours. The reaction mixture was allowed to cool, then purified by silica gel chromatography to give 8-cyclopentyl-6-(1-ethoxy-vinyl)-5-methyl-2-(3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-6′-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one as a yellow solid (0.180 mg, 59.2%). 1H NMR δvvv (400 MHz, CDCl3) 8.73 (s, 1H), 8.16 (d, J=9.0 Hz, 1H), 8.05 (s, 1H), 8.01 (d, J=2.9 Hz, 1H), 7.36 (dd, J=2.9, 9.3 Hz, 1H), 5.90 (m, 1H), 4.52 (d, J=2.4 Hz, 1H), 4.18 (d, J=2.2 Hz, 1H), 3.93 (q, J=7.1 Hz,2H), 3.14 (m, 4H), 2.41 (s, 3H), 2.36 (m, 2H), 2.06 (m, 2H), 1.84 (m, 2H), 1.56-1.77 (m, 8H), 1.21 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureto reflux for 2 hours
  2. temperatureto cool
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-b29ac6bf07974a36893dd9d7ce2e53cb
Source dataset
uspto-grants-2008_11
Patent number
US07456168B2

Linked notes

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