Sodium Carbonate → HCID 19810627, compound

HRID 373536Notes

Reaction equation

HRID 373536 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH3:18])[N:5]=[C:4]([C:19]2[CH:28]=[CH:27][C:26]3[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=3[N:20]=2)[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].CO>[CH3:18][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][C:8]=1[C:6]1[CH:7]=[CH:2][N:3]=[C:4]([C:19]2[CH:28]=[CH:27][C:26]3[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=3[N:20]=2)[N:5]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 19810625HCID 19810625, compound

Product 1

HCID 19810627HCID 19810627, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

50 mg of palladium on charcoal (5%) were added to a suspension of 2.0 g (0.0052 mol) of 4-chloro-6-(methylnapth-2-yl)-2-(5,6,7,8-tetrahydroquinolin-2-yl)-pyrimidine and 0.64 g (0.006 mol) of sodium carbonate in 150 ml of absolute methanol, under argon. The mixture was stirred vigorously for 16 hours at 25° C. under a hydrogen atmosphere. The solid was filtered off, the filtrate was concentrated, and the residue was subjected to flash chromatography (silica gel/ethyl acetate). 1.3 g (71%) of a white solid of melting point 156° C. to 158° C. are obtained.

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-fa0ecb92486a4803b7f1c05b820780cc
Source dataset
uspto-grants-1992_11
Patent number
US05164393

Reaction notes

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