Sodium Acetate → methyl 4-(2-amino-4-oxo-1,7-dihydropyrrolo[2,3-d]pyrimidin-6-yl)benzoate

HRID 590622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 590622
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([NH2:9])[N:3]=1.C([O-])(=O)C.[Na+].Br[CH2:16][C:17]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)=O>O.CO>[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]2[CH:16]=[C:17]([C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=3)[NH:9][C:4]=2[N:3]=1

Komponenten

6

Edukt 3

HCID 517045Sodium AcetateHCID 13612771Methyl 4-(2-bromoacetyl)benzoateHCID 178507952HCID 178507952, Verbindung

Produkt 1

HCID 178497455methyl 4-(2-amino-4-oxo-1,7-dihydropyrrolo[2,3-d]pyrimidin-6-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 2,6-diamino-4-hydroxypyrimidine (CAS: 56-06-4, 1 g, 7.93 mmol) and sodium acetate (0.85 g, 10.32 mmol) in water (180 mL) was stirred at 100° C. for 30 minutes. Methyl 4-(2-bromoacetyl)benzoate (2.24 g, 8.72 mmol) was suspended in MeOH (25 mL) and was added slowly to the above solution. The reaction mixture was then stirred at 100° C. for 16-20 h and then cooled to room temperature. The residue was filtered and dried. It was then stirred in CH2Cl2 (10 mL) and filtered to provide XI-8-I (1.07 g, 47.5%). LCMS: m/z 285 (M+1)+.

Aufarbeitung

  1. additionwas added slowly to the above solution
  2. temperaturecooled to room temperature
  3. filtrationThe residue was filtered
  4. customdried
  5. stirringIt was then stirred in CH2Cl2 (10 mL)
  6. filtrationfiltered
  7. customto provide XI-8-I (1.07 g, 47.5%)

Quellen und Nachweise

ORD-Eintrag
ord-703ecf938d9e4e6e9c0f5c3874ceb07c
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233983B2

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