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

HRID 864788

反応式

HRID 864788 の反応式
[N:1]1([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:21][C:22]([C:24]1[CH:35]=[CH:34][C:27]([O:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:25]=1)=[O:23]>C(#N)C>[N:10]1[CH:11]=[CH:12][C:7]([N:1]2[CH2:6][CH2:5][N:4]([CH2:21][C:22]([C:24]3[CH:35]=[CH:34][C:27]([O:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:25]=3)=[O:23])[CH2:3][CH2:2]2)=[N:8][CH:9]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 243438Methyl 4-bromoacetylphenoxyacetateHCID 183211374-(Piperazin-1-yl)pyrimidine

生成物 1

HCID 18918603Methyl 4-[2-[4-(4-pyrimidinyl)piperazin-1-yl]acetyl]phenoxyacetate収率 26.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-cdecd2a4a6604fe7835629cb99d3333c
出典データセット
uspto-grants-1996_10
特許番号
US05563141

関連ノート

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