Sodium Bicarbonate → 2-Amino-4-(4-benzyloxy-2-methyl-phenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

HRID 1161731

Reaktionsgleichung

Reaktionsgleichung von HRID 1161731
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1B(O)O.[CH2:19]([O:21][C:22]([C:24]1[S:34][C:27]2[N:28]=[C:29]([NH2:33])[N:30]=[C:31](Cl)[C:26]=2[CH:25]=1)=[O:23])[CH3:20].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:19]([O:21][C:22]([C:24]1[S:34][C:27]2[N:28]=[C:29]([NH2:33])[N:30]=[C:31]([C:3]3[CH:4]=[CH:5][C:6]([O:8][CH2:9][C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)=[CH:7][C:2]=3[CH3:1])[C:26]=2[CH:25]=1)=[O:23])[CH3:20]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 27732454-Benzyloxy-2-methylphenylboronic acidHCID 16096301Ethyl 2-amino-4-chlorothieno(2,3-d)pyrimidine-6-carboxylate

Produkt 1

HCID 112009432-Amino-4-(4-benzyloxy-2-methyl-phenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl esterAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-methyl-4-benzyloxyphenylboronic acid (225 mg; 0.93 mmol) was added to 2-Amino-4-chloro-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (example 1; step 1) (200 mg; 0.776 mmol) in DMF (10 mL). NaHCO3 (1.0M aq. Solution; 2.33 mL) was added and mixture degassed with N2. Pd(PPh3)2Cl2 was added and reaction mixture heated at 80 degrees C. for 5 hours Reaction mixture was allowed to cool to room temperature and DMF removed in vacuo. The residue was partitioned between ethyl acetate (50 mL) and sat. NaCl (aq) (50 mL) Organic phase was dried over Na2SO4 and filtered, filtrate solvents removed in vacuo to afford a yellow oil which was purified by ion-exchange chromatography (IST SCX-2 column) to afford product as a brown-yellow solid (230 mg; 71%)

Aufarbeitung

  1. custommixture degassed with N2
  2. additionPd(PPh3)2Cl2 was added
  3. customreaction mixture
  4. customfor 5 hours Reaction mixture
  5. temperatureto cool to room temperature
  6. customDMF removed in vacuo
  7. customThe residue was partitioned between ethyl acetate (50 mL) and sat. NaCl (aq) (50 mL) Organic phase
  8. dry with materialwas dried over Na2SO4
  9. filtrationfiltered
  10. customfiltrate solvents removed in vacuo
  11. customto afford a yellow oil which
  12. customwas purified by ion-exchange chromatography (IST SCX-2 column)

Quellen und Nachweise

ORD-Eintrag
ord-3e6731320f7e48c19f5587eaabd46a8b
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820658B2

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