Triethylamine → Methyl 4-[2-[4-(4-pyrimidinyl)piperazin-1-yl]acetyl]phenoxyacetate

To a mixture of 4-(1-piperazinyl)pyrimidine (preparation described in DE 2316920) (1.57 g) and triethylamine (3.87 g) in acetonitrile (40 ml) at room temperature was added dropwise over about 0.5 hour a solution of methyl 4-bromoacetylphenoxyacetate (2.73 g) in acetonitrile (25 ml). On completion of the addition the reaction mixture was stirred at room temperature for 2 days. The precipitated solid was filtered off, washed with acetonitrile and the combined filtrate and washings evaporated to dryness. The resultant red oil was purified by flash chromatography, first on silica by elution with 1-5% v/v methanol/dichloromethane, then on neutral alumina by elution with 3% v/v methanol/dichloromethane, to yield the title compound (0.92 g) as an off-white solid: NMR (CDCl3) δ2.69 (4H, m), 3.72 (4H, m), 3.80 (2H, s), 3.82 (3H, s), 4.71 (2H, s), 6.49 (1H, m), 6.94 (2H, d), 8.01 (2H, d), 8.20 (1H, d), 8.60 (1H, s); m/Z 371 (M+H)+ ; calculated for C19H22N4O4. 0.4 H2O: C 60.4%; H, 6.09%; N, 14.8%; found: C, 60.7%; H, 6.2%; N, 14.7%.

1. additionOn completion of the addition the reaction mixture
2. filtrationThe precipitated solid was filtered off
3. washwashed with acetonitrile
4. customthe combined filtrate and washings evaporated to dryness
5. customThe resultant red oil was purified by flash chromatography, first on silica by elution with 1-5% v/v methanol/dichloromethane
6. washon neutral alumina by elution with 3% v/v methanol/dichloromethane

ORD-Eintrag

ord-cdecd2a4a6604fe7835629cb99d3333c

Quelldatensatz

uspto-grants-1996_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05563141