HCID 9886228, compound → HCID 9969243, compound

HRID 2298428Notes

Reaction equation

HRID 2298428 reaction equation
[CH2:1]([CH:3]([N:6]1[CH2:11][C:10](=O)[N:9]([CH3:13])[C:8]2[C:14]([O:19][C:20]3[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=3[CH3:28])=[N:15][C:16]([CH3:18])=[CH:17][C:7]1=2)[CH2:4][CH3:5])[CH3:2].CSC.B>C1COCC1>[CH2:1]([CH:3]([N:6]1[CH2:11][CH2:10][N:9]([CH3:13])[C:8]2[C:14]([O:19][C:20]3[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=3[CH3:28])=[N:15][C:16]([CH3:18])=[CH:17][C:7]1=2)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 9886228HCID 9886228, compoundHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 9969243HCID 9969243, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1-(1-Ethyl-propyl)-4,7-dimethyl-5-(2,4,6-trimethyl-phenoxy)-1,4-dihydro-2H-pyrido[3,4-b]pyrazin-3-one (21 mg, 0.055 mmol) and 2 M borane dimethylsulfide complex (BH3•DMS) (0.07 ml, 0.14 mmol) in 2 ml of dry THF was heated at reflux for 3 hours. The mixture was cooled to 0° C. and quenched with 0.2 ml of meoh and 0.2 ml of concentrated hydrochloric acid (HCl). The resulting mixture was stirred at room temperature for 2 hours and concentrated to dryness. The residue was quenched with water and extracted with chloroform. The organic layer was dried and concentrated to give 19 mg of a clear oil that was purified through silica gel column chromatography using 10% ethyl acetate in hexane as eluent to give 11 mg of the title compound as white crystals, mp 78-80° C.; 1H NMR (CDCl3) δ 6.85(s,2H), 6.28(s,1H), 3.73(m,1H), 3.12 (m,4H), 2.85(s,3H), 2.29(s,3H), 2.,13(s,3H), 2.11 (s,6H), 1.61(m,4H), 0.90(t,6H) ppm.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customquenched with 0.2 ml of meoh and 0.2 ml of concentrated hydrochloric acid (HCl)
  4. concentrationconcentrated to dryness
  5. customThe residue was quenched with water
  6. extractionextracted with chloroform
  7. customThe organic layer was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bcf32a1a27a74e92b0dc53b4cb210119
Source dataset
uspto-grants-2002_12
Patent number
US06492520B1

Reaction notes

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