Triethylamine → Methyl 2-(cyclopentyl(5-formyl-2-(methylthio)pyrimidin-4-yl)amino)acetate

HRID 875971Notes

Reaction equation

HRID 875971 reaction equation
C(N(CC)CC)C.Cl[C:9]1[C:14]([CH:15]=[O:16])=[CH:13][N:12]=[C:11]([S:17][CH3:18])[N:10]=1.[CH:19]1([NH:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:23][CH2:22][CH2:21][CH2:20]1.C(=O)(O)[O-].[Na+]>C1COCC1>[CH:19]1([N:24]([C:9]2[C:14]([CH:15]=[O:16])=[CH:13][N:12]=[C:11]([S:17][CH3:18])[N:10]=2)[CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22080509Methyl 2-(cyclopentylamino)acetateHCID 594193864-Chloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

Product 1

HCID 58299719Methyl 2-(cyclopentyl(5-formyl-2-(methylthio)pyrimidin-4-yl)amino)acetateYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (10.9 mL, 78.2 mmol) was added to a solution of compound 224 (12.3 g, 65.2 mmol) and compound 225 (12.8 g, 81.5 mmol) in THF (200 mL). The reaction was stirred at room temperature. After 6 h, the reaction contents were poured into saturated sodium bicarbonate and extracted with ethyl acetate. The combined organics were dried over MgSO4 and concentrated in vacuo. The crude material was crystallized from ethyl acetate and hexanes to afford methyl 2-(cyclopentyl(5-formyl-2-(methylthio)pyrimidin-4-yl)amino)acetate (226) (17.55 g, 87.0% yield).

Workup

  1. customthe reaction contents
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organics were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was crystallized from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-9621080f961948b0bc12b0f9d513aa57
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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