Potassium Carbonate → HCID 59643132, compound

HRID 2251476Notes

Reaction equation

HRID 2251476 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:4]=1[CH2:5][NH:6][CH2:7][CH2:8][C:9]1[CH:22]=[CH:21][C:12]([O:13][C:14]([CH3:20])([CH3:19])[C:15]([O:17]C)=[O:16])=[CH:11][CH:10]=1.Cl[C:34]1[N:39]=[CH:38][C:37]([CH2:40][CH2:41][CH3:42])=[CH:36][N:35]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[F:31][C:2]([F:32])([F:1])[C:3]1[CH:26]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:24]=[CH:23][C:4]=1[CH2:5][N:6]([C:34]1[N:39]=[CH:38][C:37]([CH2:40][CH2:41][CH3:42])=[CH:36][N:35]=1)[CH2:7][CH2:8][C:9]1[CH:22]=[CH:21][C:12]([O:13][C:14]([CH3:20])([CH3:19])[C:15]([OH:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27357842-Chloro-5-propylpyrimidineHCID 59643248HCID 59643248, compound

Product 1

HCID 59643132HCID 59643132, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Condensation of methyl 2-[4-(2-{[2,4-bis(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (250 mg; 0.54 mmol) with 2-chloro-5-propyl-pyrimidine (85 mg; 0.54 mmol) as per general procedure E (1.25 eq. K2CO3, dioxane, 220C, 15 hr) was accompanied by partial ester hydrolysis and afforded the title compound in low yield. For ease of purification, the carboxylic acid was converted to its methyl ester derivative (using a standard trimethylsilyldiazomethane/MeOH protocol), chromatographed and subjected to the base-mediated hydrolysis procedure H to afford the title compound in 17% yield (29 mg).

Sources & evidence

ORD record
ord-a603c4cfcefb4b1dac6c61f1148ee291
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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