Hydrochloric Acid → Pyrido-[2,3-d]-pyrimidin-7-one 58

HRID 1272000Notes

Reaction equation

HRID 1272000 reaction equation
[CH:1]1([N:6]2[C:11]3[N:12]=[C:13]([NH:16][C:17]4[N:22]=[CH:21][C:20]([N:23]5[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]5)=[CH:19][CH:18]=4)[N:14]=[CH:15][C:10]=3[C:9]([CH3:29])=[C:8]([C:30]([O:32]CC)=[CH2:31])[C:7]2=[O:35])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>C(OCC)(=O)C.ClCCl.C([O-])(O)=O.[Na+]>[C:30]([C:8]1[C:7](=[O:35])[N:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:11]2[N:12]=[C:13]([NH:16][C:17]3[N:22]=[CH:21][C:20]([N:23]4[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]4)=[CH:19][CH:18]=3)[N:14]=[CH:15][C:10]=2[C:9]=1[CH3:29])(=[O:32])[CH3:31]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 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-one

Product 1

HCID 5330301Pyrido-[2,3-d]-pyrimidin-7-one 58Yield 71%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

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 (0.180 g, 0.379 mmol) was dissolved in ethyl acetate (10 mL) and 6 N HCl (10 mL) was added then the mixture was stirred at room temperature for 2 hours. The mixture was diluted with dichloromethane and aqueous NaHCO3. The layers were separated and the organic layer was dried over MgSO4, filtered, and the solvent evaporated to give 6-acetyl-8-cyclopentyl-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 (0.120 g, 71.0%). 1H NMR δ (400 MHz, CDCl3) 8.78 (s, 1H), 8.20 (d, J=8.5 Hz, 1H), 7.95 (s, 1H), 7.39 (m, 1H), 5.85 (m, 1H), 3.15 (m, 4H), 2.53 (s, 3H), 2.36 (s, 3H), 2.33 (m, 2H), 2.05 (m, 2H), 1.87 (m, 2H), 1.77–1.56 (m, 8H). MS (APCI); M++1: Calc'd, 447.2, Found 447.2. Anal. Calc'd for C25H30N6O2 0.35 H2O: C, 66.31; H, 6.83; N, 18.56. Found: C, 66.68; H, 6.76; N, 18.07.

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-c9cc41b330ed411d84bf5c47e27a2f74
Source dataset
uspto-grants-2007_04
Patent number
US07208489B2

Reaction notes

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