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

HRID 1040901

반응식

HRID 1040901 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f5fff7ba29584c36a30311c4ce750b5e
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552186B2

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