Water → HCID 59506448, compound

HRID 1798902Notes

Reaction equation

HRID 1798902 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[CH2:13]([N:20]([CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:21]1[C:26]([C:27]([O:29]CC)=O)=[C:25]([Cl:32])[N:24]=[C:23]([S:33][CH3:34])[N:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>O1CCCC1>[CH2:13]([N:20]1[C:21]2[N:22]=[C:23]([S:33][CH3:34])[N:24]=[C:25]([Cl:32])[C:26]=2[C:27](=[O:29])[CH:36]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:35]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7912DiisopropylamineHCID 59506569HCID 59506569, compoundHCID 178418339Butyllithium

Product 1

HCID 59506448HCID 59506448, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled solution at 0° C. of diisopropylamine (51.0 mL, 0.361 mol) in tetrahydrofuran (600 mL) was added n-BuLi (221 mL, 0.353 mol, 1.6 M in hexane) dropwise and the mixture was stirred at the 0° C. for 45 min. The reaction mixture was then cooled to −78° C. and a solution of ethyl 4-(benzyl(3-ethoxy-3-oxopropyl)amino)-6-chloro-2-(methylthio)pyrimidine-5-carboxylate (50 g, 0.114 mol) in tetrahydrofuran (500 mL) was added drop wise over 45 min. The reaction mixture was stirred at -78° C. for 15 min before water (1 L) was added. The reaction mixture was then warmed to room temperature and the organic phase was separated from the aqueous layer. The aqueous layer was extracted with EtOAc (500 mL). The combined organic layers were washed with water (1 L), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude ethyl 8-benzyl-4-chloro-2-(methylthio)-5-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-6-carboxylate that was used for next step directly.

Workup

  1. temperatureThe reaction mixture was then cooled to −78° C.
  2. additionwas added
  3. temperatureThe reaction mixture was then warmed to room temperature
  4. customthe organic phase was separated from the aqueous layer
  5. extractionThe aqueous layer was extracted with EtOAc (500 mL)
  6. washThe combined organic layers were washed with water (1 L)
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9244a00eb61c4e4ca31266a354d71924
Source dataset
uspto-grants-2013_01
Patent number
US08343983B2

Reaction notes

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