Potassium Carbonate → Methyl 6-{[5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoate

HRID 1926902Notes

Reaction equation

HRID 1926902 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:9][O:8][C:4]=2[N:5]=[CH:6][N:7]=1.Cl.[CH3:20][O:21][C:22](=[O:29])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][NH2:28].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:20][O:21][C:22](=[O:29])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:9][O:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11499324Methyl 6-aminohexanoate hydrochlorideHCID 580168144-Chloro-5-(4-methoxyphenyl)furo[2,3-d]pyrimidine

Product 1

HCID 25124063Methyl 6-{[5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dissolve 7.1 g (27.2 mol) 4-chloro-5-(4-methoxyphenyl)furo[2,3-d]pyrimidine in 250 ml acetonitrile and add 5.9 g (32.7 mmol) 6-aminohexanoic acid methyl ester hydrochloride and 9.4 g (68.1 mmol) potassium carbonate. Heat the mixture under reflux for 18 hours and then filter after cooling to room temperature. Mix the residue three times in 50 ml water each time, filter and dry under vacuum. 4.1 g (41% of theor.) of the title compound is obtained.

Workup

  1. temperatureHeat the mixture
  2. temperatureunder reflux for 18 hours
  3. filtrationfilter
  4. additionMix the residue three times in 50 ml water each time
  5. filtrationfilter
  6. customdry under vacuum

Sources & evidence

ORD record
ord-ec0c4ee0d2fe48ff80e26ee909d38364
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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