4-Amino-5-pyrimidinecarboxamide → HCID 135923522, Verbindung

HRID 2076817

Reaktionsgleichung

Reaktionsgleichung von HRID 2076817
[NH2:1][C:2]1[C:7]([C:8]([NH2:10])=[O:9])=[CH:6][N:5]=[CH:4][N:3]=1.CO[C:13](=O)[CH2:14][O:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[F:24][C:20]1[CH:19]=[C:18]([CH2:17][CH2:16][O:15][CH2:14][C:13]2[NH:10][C:8](=[O:9])[C:7]3[C:2]([N:1]=2)=[N:3][CH:4]=[N:5][CH:6]=3)[CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 8182124-Amino-5-pyrimidinecarboxamideHCID 2733832Lithium HexamethyldisilazideHCID 67099252HCID 67099252, Verbindung

Produkt 1

HCID 135923522HCID 135923522, VerbindungAusbeute 1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A suspension of the commercially available 4-amino-5-pyrimidinecarboxamide [4786-51-0] (150 mg, 1.09 mmol) and of [2-(3-fluoro-phenyl)-ethoxy]-acetic acid methyl ester (254 mg, 1.19 mmol) in THF (7 ml) was treated with LiHMDS (1M solution in THF, 2.17 ml) and stirred overnight at ambient temperature. The resulting yellow suspension was filtered and the filtrate was evaporated to dryness and triturated with EtOAc/MeOH 9:1. The yellow solid was filtered off, the mother-liquid was evaporated and the remaining residue was purified by column chromatography (silica gel, EtOAc/MeOH, 9:1) to give the title compound as a white solid (3 mg, 1%), MS: m/e=301.1 [M+H+].

Aufarbeitung

  1. filtrationThe resulting yellow suspension was filtered
  2. customthe filtrate was evaporated to dryness
  3. customtriturated with EtOAc/MeOH 9:1
  4. filtrationThe yellow solid was filtered off
  5. customthe mother-liquid was evaporated
  6. customthe remaining residue was purified by column chromatography (silica gel, EtOAc/MeOH, 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-774e415be8b145c5b0dc18578322c24b
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928106B2

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