Potassium Carbonate → HCID 57962572, compound

HRID 541568Notes

Reaction equation

HRID 541568 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[C:11]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[CH:12][C:13]([CH3:24])=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:15]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:37][C:38]1[N:43]=[C:42](Cl)[C:41]([Cl:45])=[CH:40][N:39]=1>CN(C)C=O.C(=O)(O)[O-].[Na+]>[Cl:37][C:38]1[N:43]=[C:42]([NH:1][C:2]2[CH:3]=[C:4]([CH2:8][CH2:9][C:10]3[C:11]([N:25]4[CH2:26][CH2:27][O:28][CH2:29][CH2:30]4)=[CH:12][C:13]([CH3:24])=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH:15]=3)[CH:5]=[CH:6][CH:7]=2)[C:41]([Cl:45])=[CH:40][N:39]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 57962576HCID 57962576, compound

Product 1

HCID 57962572HCID 57962572, compoundYield 26.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

tert-Butyl {5-[2-(3-aminophenyl)ethyl]-2-methyl-4-morpholin-4-ylphenyl}carbamate (31 mg, 0.08 mmol) and potassium carbonate (16 mg, 0.11 mmol) were stirred in N,N-dimethylformamide (1 mL) and 2,4,5-trichloropyrimidine (9 μL, 0.08 mmol) was added. The mixture was stirred for 16 hours (or 16 h) and diluted with saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate and evaporated to give the desired compound (12 mg, 14%). LCMS for C28H34NCl2N3O3 (M+H)+: m/z=558.1.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. customevaporated

Sources & evidence

ORD record
ord-8d5efd8f5da34414947cecb991ee36b0
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

Loading…