Triethylamine → Ethyl 4-hydrazinyl-2-(methylthio)-5-oxo-8-phenyl-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-6-carboxylate

HRID 1798899Notes

Reaction equation

HRID 1798899 reaction equation
Cl[C:2]1[C:3]2[C:13](=[O:14])[CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][N:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:4]=2[N:5]=[C:6]([S:8][CH3:9])[N:7]=1.C(N(CC)CC)C.O.[NH2:34][NH2:35]>O1CCOCC1>[NH:34]([C:2]1[C:3]2[C:13](=[O:14])[CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][N:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:4]=2[N:5]=[C:6]([S:8][CH3:9])[N:7]=1)[NH2:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 59506342Ethyl 4-chloro-2-(methylthio)-5-oxo-8-phenyl-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 59506527Ethyl 4-hydrazinyl-2-(methylthio)-5-oxo-8-phenyl-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-6-carboxylateYield 96.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of ethyl 4-chloro-2-(methylthio)-5-oxo-8-phenyl-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-6-carboxylate (21 g, 55.57 mmol) in 1,4-dioxane (400 mL) was added triethylamine (8.52 mL, 61.13 mmol) followed by hydrazine hydrate (3.06 g, 61.13 mmol). The reaction mixture was stirred at room temperature for 5-6 h. Upon completion of the reaction, dioxane was removed under reduced pressure and water (250 mL) was added to the reaction mixture. The reaction mixture was then extracted with dichloromethane (200 mL×3). The combined organic layers was washed with water (500 mL) followed by brine (500 mL), dried over anhydrous Na2SO4, filtered and concentrated to give crude ethyl 4-hydrazinyl-2-(methylthio)-5-oxo-8-phenyl-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-6-carboxylate (20 g) which was used in the next step without purification. LCMS [M+H]: 374

Workup

  1. customwas removed under reduced pressure and water (250 mL)
  2. additionwas added to the reaction mixture
  3. extractionThe reaction mixture was then extracted with dichloromethane (200 mL×3)
  4. washThe combined organic layers was washed with water (500 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9dade497f401400891085d5ca438a049
Source dataset
uspto-grants-2013_01
Patent number
US08343983B2

Reaction notes

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