Chlorotrimethylsilane → HCID 178474807, Verbindung

HRID 1106112

Reaktionsgleichung

[C:1]([NH:4][CH2:5][CH2:6][C:7](O)=[O:8])(=[O:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:37]=[C:36]([OH:38])[C:35]([C:39]([OH:41])=[O:40])=[CH:34][N:33]=2)=[CH:28][CH:27]=1.C(N(CC)CC)C.C[Si](Cl)(C)C>ClCCl.C(#N)C>[C:1]([NH:4][CH2:5][CH2:6][C:7]([NH:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[N:37]=[C:36]([OH:38])[C:35]([C:39]([OH:41])=[O:40])=[CH:34][N:33]=2)=[CH:30][CH:31]=1)=[O:8])(=[O:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: -10 °C

Versuchsvorschrift

A solution of 4.6 g (35 mmol) of N-acetyl-beta-alanine, 100 ml acetonitrile, and 3.9 ml (35 mmol) of N-methylmorpholine is stirred at -15° C. and 5.0 ml (38.5 mmol) of isobutyl chloroformate is added. After 30 minutes at -15° C. a solution prepared from 4.05 g (17.5 mmol) of 2-(4-aminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid, 7.35 ml (52.5 mmol) of triethylamine, and 7.96 ml (62.7 mmol) of trimethylsilyl chloride in 100 ml of dichloromethane is added and the mixture stirred at -10° C. for 1 hour and at room temperature overnight. The mixture is evaporated to near dryness in vacuo and treated with 200 ml of water. The product is precipitated by acidifying to pH 2.0 and is filtered, washed with water, isopropanol, ether, and dried to give 5.8 g of 2-[4-(N-acetyl-beta-alanylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid.

Aufarbeitung

additionis added
customThe mixture is evaporated
additiontreated with 200 ml of water
customThe product is precipitated
filtrationis filtered
washwashed with water, isopropanol, ether
customdried

Quellen und Nachweise

ORD-Eintrag: ord-2899a12b1d5040b5941ba4b0bcb1bad2
Quelldatensatz: uspto-grants-1982_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04311699

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