Sodium t-butoxide → 2-Pyrrolidin-1-yl-4-p-tolyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester

HRID 72801Notes

Reaction equation

HRID 72801 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH:10]([C:15](=O)[C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.[N:31]1([C:36]([NH2:38])=[NH:37])[CH2:35][CH2:34][CH2:33][CH2:32]1.CC(C)([O-])C.[Na+]>CC(O)(C)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:37]=[C:36]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[N:38]=[C:15]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 23676156Sodium t-butoxideHCID 67370060Pyrrolidine-1-carboxamidine trifluoroacetateHCID 673723323-(4-Methyl-benzoyl)-4-oxo-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 673698102-Pyrrolidin-1-yl-4-p-tolyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl esterYield 36.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a mixture of 3-(4-Methyl-benzoyl)-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (0.24 g, 0.74 mmol) and pyrrolidine-1-carboxamidine trifluoroacetate (0.14 g, 0.58 mmol) in t-BuOH (7.5 mL) was added sodium tert-butoxide (0.10 g, 1.1 mmol). The mixture was heated at reflux for 2 h, then cooled to rt, diluted with H2O and extracted with CH2Cl2 (2×). The combined organic extracts were dried and concentrated. The residue was purified by FCC to give the title compound (0.084 g, 29%) as a clear oil. MS (ESI): mass calcd. for C23H30N4O2, 394.5; m/z found, 395.5 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. extractionextracted with CH2Cl2 (2×)
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated
  6. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-805c9fc3f1c040e096cbd139ab11fe2e
Source dataset
uspto-grants-2014_09
Patent number
US08829011B2

Reaction notes

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