Potassium Carbonate → HCID 178483099, compound

HRID 510228Notes

Reaction equation

HRID 510228 reaction equation
C([O-])([O-])=O.[K+].[K+].S(O)(O)(=O)=O.[CH3:12][N:13]([CH3:17])[C:14]([NH2:16])=[NH:15].[C:18]([N:25]1[CH2:30][CH2:29][CH:28]([C:31](OCC)=[O:32])[C:27](=O)[CH2:26]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[Al]>CO.O>[CH3:12][N:13]([CH3:17])[C:14]1[N:16]=[C:31]([OH:32])[C:28]2[CH2:29][CH2:30][N:25]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:26][C:27]=2[N:15]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 220673Guanidine, 1,1-dimethyl-, sulfateHCID 5359268AluminumHCID 158529891-tert-Butyl 4-ethyl 3-oxopiperidine-1,4-dicarboxylate

Product 1

HCID 178483099HCID 178483099, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

K2CO3 (563 mg, 4.07 mmol) and 1,1-dimethylguanidine sulfate (566 mg, 2.04 mmol) were added to a suspension of ethyl N—BOC-3-oxopiperidine-4-carboxylate in MeOH (2 mL) and H2O (1 mL) in a 40 mL vial. The reaction was heated in an aluminium block at 70° C. for 90 minutes. LCMS analysis showed that the reaction was complete. The mixture was acidified to pH 3 and extracted with DCM (3×). The combined organic extracts were dried over MgSO4, filtered and concentrated to obtain tert-butyl 2-(dimethylamino)-4-hydroxy-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate as a pale yellow solid which was used without further purification. MS (ESI): mass calcd. for C14H22N4O3, 294.3. m/z found, 295.3 [M+H]+. 1H NMR (400 MHz, MeOD) δ 4.29-4.11 (m, 2H), 3.71-3.46 (m, 2H), 3.09 (s, 6H), 2.42 (t, J=5.8 Hz, 2H), 1.58-1.38 (m, 9H).

Workup

  1. extractionextracted with DCM (3×)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-848351dae9b74df2a6cbc8bf0d055988
Source dataset
uspto-grants-2015_08
Patent number
US09096596B2

Reaction notes

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