Water → (2,5-Dichloro-pyrimidin-4-yl)-(3-morpholin-4-yl-phenyl)-amine

HRID 1040901

反応式

HRID 1040901 の反応式
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[O:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=2)[NH2:25])[CH2:18][CH2:17]1.O>O1CCCC1.ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([NH:25][C:24]2[CH:26]=[CH:27][CH:28]=[C:22]([N:19]3[CH2:20][CH2:21][O:16][CH2:17][CH2:18]3)[CH:23]=2)[C:5]([Cl:9])=[CH:4][N:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 8477683-(Morpholin-4-yl)aniline

生成物 1

HCID 86633892(2,5-Dichloro-pyrimidin-4-yl)-(3-morpholin-4-yl-phenyl)-amine

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

2,4,5-Trichloropyrimidine (0.960 g, 5.2 mmol) was dissolved in tetrahydrofuran (20 mL). Potassium carbonate (1.20 g, 8.70 mmol) was added, followed by 3-morpholinoaniline (0.875 g, 4.90 mmol). After stirring overnight, water (30 mL) and dichloromethane (30 mL) were added, the phases separated and the aqueous layer extracted once with dichloromethane (30 mL). The combined organic fractions were dried over sodium sulfate, concentrated onto silica gel and chromatographed (120 g SiO2, 0-50% EA:Hex). (2,5-Dichloro-pyrimidin-4-yl)-(3-morpholin-4-yl-phenyl)-amine was isolated as an off-white solid (1.16 g, 73%). m.p.=142-145° C.; LCMS (m/e) 325 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 8.20 (s, 1H), 7.38 (s, 1H), 7.28 (m, 1H), 7.21 (s, 1H), 7.01 (d, 1H, J=7.8 Hz), 6.75 (d, 1H, J=8.4 Hz), 3.88 (t, 4H, J=4.8 Hz), 3.21 (t, 4H, J=4.8 Hz).

後処理

  1. customthe phases separated
  2. extractionthe aqueous layer extracted once with dichloromethane (30 mL)
  3. dry with materialThe combined organic fractions were dried over sodium sulfate
  4. concentrationconcentrated onto silica gel
  5. customchromatographed (120 g SiO2, 0-50% EA:Hex)

出典と根拠

ORDレコード
ord-f5fff7ba29584c36a30311c4ce750b5e
出典データセット
uspto-grants-2013_10
特許番号
US08552186B2

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