Hydrochloric Acid → 8-Indan-5-yl-2-methylsulfanyl-5-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

HRID 12331Notes

Reaction equation

HRID 12331 reaction equation
[Na].N#N.C(O[C:7]([C:9]1[C:10]([N:17]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[CH2:23][CH2:22][CH2:21]3)=[N:11][C:12]([S:15][CH3:16])=[N:13][CH:14]=1)=[O:8])C.CC(C)([O-])C.[Na+].Cl>C1(C)C=CC=CC=1.C(O)(C)(C)C>[CH2:32]([O:31][C:29]([CH:28]1[CH2:27][N:17]([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[CH2:23][CH2:22][CH2:21]3)[C:10]2[N:11]=[C:12]([S:15][CH3:16])[N:13]=[CH:14][C:9]=2[C:7]1=[O:8])=[O:30])[CH3:33]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 5360545SodiumHCID 23676156Sodium t-butoxideHCID 252228764-[(2-Ethoxycarbonyl-ethyl)-indan-5-yl-amino]-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 252228778-Indan-5-yl-2-methylsulfanyl-5-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

To sodium (25 wt % dispersion in paraffin wax, 1.6 g, 16.9 mmol) was added t-butanol (30 mL) under stirring and N2. After 10 minutes, a solution of 4-[(2-ethoxycarbonyl-ethyl)-indan-5-yl-amino]-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (6.6 g, 15.4 mmol) in 40 mL of toluene was added to the sodium t-butoxide solution. The mixture was then heated at 90° C. for 30 minutes. The solution was cooled and poured into crushed ice. The solution was adjusted to pH 7 using HCl solution. The precipitates were extracted into EtOAc twice. The solvent was evaporated under vacuum and the product (bright yellow solid, 4 g, 62%) was recrystallized from isopropanol. 1H NMR (300 MHz, CDCl3) indicated that the presence of both enol and keto forms in a 4:1 ratio.

Workup

  1. temperatureThe solution was cooled
  2. additionpoured
  3. custominto crushed ice
  4. extractionThe precipitates were extracted into EtOAc twice
  5. customThe solvent was evaporated under vacuum
  6. customthe product (bright yellow solid, 4 g, 62%) was recrystallized from isopropanol

Sources & evidence

ORD record
ord-97b2d45e987f4f5581a86c3d7fc3bcd7
Source dataset
uspto-grants-2010_06
Patent number
US07728003B2

Reaction notes

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