Ethyl Acetate → HCID 86663149, compound

HRID 1626537Notes

Reaction equation

HRID 1626537 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9][CH2:8][C:6]=2[N:7]=1.[CH3:20][CH2:21][N:22](C(C)C)[CH:23]([CH3:25])[CH3:24].CC[O:31]C(C)=O>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[N:3]=[C:4]([N:22]2[CH2:21][CH2:20][O:31][CH2:24][C@@H:23]2[CH3:25])[C:5]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 17998716tert-Butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Product 1

HCID 86663149HCID 86663149, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of tert-butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (1.00 g, 3.29 mmol) and DIPEA (1.21 mL, 6.97 mmol) at room temperature (20° C.) was added 3-S-methyl morpholine (0.54 g, 5.33 mmol). The reaction mixture was heated to 35° C. and stirred for 48 h. The reaction was diluted with DCM and Sat. NaHCO3. The organic layer was rinsed (brine), dried (anhydrous Na2SO4) and concentrated in vacuo. The desired product was isolated by flash chromatography (silica, 50 g, 0-50% EtOAc in petroleum ether (40-60) over 25 min) as a white solid (0.71 g, 1.92 mmol, 59% yield).

Workup

  1. washThe organic layer was rinsed (brine)
  2. dry with materialdried (anhydrous Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-805b18c4634b409b93b4a73e35278954
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

Loading…