Potassium Carbonate → HCID 178433419, compound

HRID 510229Notes

Reaction equation

HRID 510229 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl.[C:8]([NH2:11])(=[NH:10])[CH3:9].[C:12]([N:19]1[CH2:24][CH2:23][CH:22]([C:25](OCC)=[O:26])[C:21](=O)[CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[Al]>CO.O>[OH:26][C:25]1[C:22]2[CH2:23][CH2:24][N:19]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:20][C:21]=2[N:10]=[C:8]([CH3:9])[N:11]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 67170Acetamidine monohydrochlorideHCID 5359268AluminumHCID 158529891-tert-Butyl 4-ethyl 3-oxopiperidine-1,4-dicarboxylate

Product 1

HCID 178433419HCID 178433419, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

K2CO3 (535 mg, 3.87 mmol) and acetamidine hydrochloride (185 mg, 1.93 mmol) were added to a suspension of ethyl N—BOC-3-oxopiperidine-4-carboxylate (525 mg, 1.93 mmol) in MeOH (3 mL) and H2O (1 mL) in a 40 mL vial. The reaction was heated in an aluminum block at 70° C. for 90 minutes. LCMS analysis indicated complete consumption of the starting material. The reaction mixture was then acidified to pH 3 and extracted with DCM (3×). The combined organic extracts were dried over MgSO4, filtered and concentrated to obtain tert-butyl 4-hydroxy-2-methyl-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate as a yellow oil. The product was used without further purification (473 mg, 93%). MS (ESI): mass calcd. for C13H19N3O3 265.1 m/z found, 266.2[M+H]+. 1H NMR (400 MHz, CDCl3) δ 4.37 (s, 2H), 3.71-3.50 (m, 2H), 2.60 (s, 2H), 2.50-2.38 (m, 3H), 1.52-1.41 (m, 9H).

Workup

  1. customconsumption of the starting material
  2. extractionextracted with DCM (3×)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-098f6bc260114b8a8415af13d4c97400
Source dataset
uspto-grants-2015_08
Patent number
US09096596B2

Reaction notes

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