Potassium Carbonate → N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6-(3-chlorophenyl)pyrimidine-2,4-diamine

HRID 2386987노트

반응식

HRID 2386987 반응식
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[C:16](Cl)[N:15]=[C:14]([NH2:19])[N:13]=2)[CH:5]=[CH:4][N:3]=1.[Cl:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C(Cl)Cl.O>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[C:16]([C:25]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:20])[CH:26]=3)[N:15]=[C:14]([NH2:19])[N:13]=2)[CH:5]=[CH:4][N:3]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 2734323(3-Chlorophenyl)boronic acidHCID 71681979N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6-chloropyrimidine-2,4-diamine

생성물 1

HCID 44595856N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6-(3-chlorophenyl)pyrimidine-2,4-diamine

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

The product of Example 6A (69 mg, 0.246 mmol), 3-chlorophenylboronic acid (42 mg, 0.270 mmol), dichlorobis((triphenylphosphine)palladium(II) (17 mg, 0.025 mmol), and potassium carbonate (100 mg, 0.724 mmol) were combined with dioxane (5 mL) and water (1.5 mL) and heated to 100° C. overnight. The mixture was diluted with methylene chloride, washed with water, and absorbed on silica gel and purified using silica gel chromatography, eluting with a gradient of 7 N ammonia in methanol in methylene chloride (5-15%) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.98 (s, 1H) 7.76-7.86 (m, 1H) 7.61 (d, J=5.76 Hz, 1H) 7.41-7.52 (m, 2H) 7.00 (s, 1H) 6.86 (s, 1H) 6.28 (s, 1H) 6.08 (s, 2H) 5.85 (s, 2H) 5.69-5.77 (m, 1H) 3.33-3.50 (m, 4H); MS (ESI+) m/z 356.9 (M+H)+.

후처리

  1. washwashed with water
  2. customabsorbed on silica gel
  3. custompurified
  4. washeluting with a gradient of 7 N ammonia in methanol in methylene chloride (5-15%)

출처 및 근거

ORD 기록
ord-da4f9f5ed4334976a64b3289286ed8a0
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268846B2

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