4-chloro-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-2-amine → N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidine-2,4-diamine

HRID 2386978노트

반응식

HRID 2386978 반응식
Cl.Cl.[NH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[N:8]=1.Cl[C:15]1[C:16]2[CH2:26][CH2:25][CH2:24][C:23]3[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=3[C:17]=2[N:18]=[C:19]([NH2:21])[N:20]=1>COCCO.[OH-].[Na+]>[NH2:13][C:9]1[N:8]=[C:7]([NH:6][CH2:5][CH2:4][NH:3][C:15]2[C:16]3[CH2:26][CH2:25][CH2:24][C:23]4[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=4[C:17]=3[N:18]=[C:19]([NH2:21])[N:20]=2)[CH:12]=[CH:11][N:10]=1

참가 물질

5

반응물 2

HCID 866218984-chloro-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-2-amineHCID 86638141N4-(2-aminoethyl)pyrimidine-2,4-diamine dihydrochloride

생성물 1

HCID 44609408N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidine-2,4-diamine

시약·촉매·용매 2

HCID 80192-Methoxyethanol용매HCID 14798Sodium Hydroxide용매

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온도
130 °C

실험 절차

The product of Example 1E (155 mg, 0.686 mmol) and the product of Example 1C (140 mg, 0.571 mmol) were combined in 2-methoxyethanol (0.8 mL) and heated to 130° C. for three hours. The mixture was diluted with 1 N aqueous sodium hydroxide and extracted twice with methylene chloride. The organic layers were combined and dried over sodium sulfate and the mixture was 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 7.62 (d, J=4.41 Hz, 1H) 7.50-7.56 (m, 1H) 7.26-7.34 (m, 2H) 7.19-7.26 (m, 1H) 6.67-6.75 (m, 1H) 5.85 (s, 2H) 5.70-5.81 (m, 4H) 3.37-3.52 (m, 4H) 2.44 (t, J=6.78 Hz, 2H) 2.08-2.18 (m, J=6.78, 6.78 Hz, 2H) 1.92-2.04 (m, 2H); MS (ESI+) m/z 363.9 (M+H)+.

후처리

  1. extractionextracted twice with methylene chloride
  2. dry with materialdried over sodium sulfate
  3. customthe mixture was absorbed on silica gel
  4. custompurified
  5. washeluting with a gradient of 7 N ammonia in methanol in methylene chloride (5-15%)

출처 및 근거

ORD 기록
ord-58741ababeab4221b9dc1aef513a1670
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268846B2

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