Triethylamine → HCID 59506412, compound

HRID 1798903Notes

Reaction equation

HRID 1798903 reaction equation
[CH2:1]([N:8]1[C:13]2[N:14]=[C:15]([S:19][CH3:20])[N:16]=[C:17](Cl)[C:12]=2[C:11](=[O:21])[CH:10]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.O.[NH2:35][NH2:36]>O1CCOCC1>[CH2:1]([N:8]1[C:13]2[N:14]=[C:15]([S:19][CH3:20])[N:16]=[C:17]([NH:35][NH2:36])[C:12]=2[C:11](=[O:21])[CH:10]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 59506448HCID 59506448, compound

Product 1

HCID 59506412HCID 59506412, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Ethyl 8-benzyl-4-chloro-2-(methylthio)-5-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-6-carboxylate from step-1 (48 g, 0.122 mol) in 1,4-dioxane (300 mL), and triethylamine (20.5 mL, 0.147 mol) was added hydrazine hydrate (6.73 g, 0.134.6 mol). The reaction mixture was stirred at room temperature for 5-6 h. After completion of the reaction, dioxane was evaporated under vacuo, and water (250 mL) was added to the reaction mixture and was extracted with dichloromethane (200 mL×3). The combined dichloromethane layer was washed with water (500 mL) followed by brine (500 mL). The dichloromethane layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give crude ethyl 8-benzyl-4-hydrazinyl-2-(methylthio)-5-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-6-carboxylate as an oil that was used for next step without further purification.

Workup

  1. customwas evaporated under vacuo, and water (250 mL)
  2. additionwas added to the reaction mixture
  3. extractionwas extracted with dichloromethane (200 mL×3)
  4. washThe combined dichloromethane layer was washed with water (500 mL)
  5. dry with materialThe dichloromethane layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4a48caf61ef8438bb256f57dea4498c1
Source dataset
uspto-grants-2013_01
Patent number
US08343983B2

Reaction notes

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