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Ethanol → 2-chloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)-6-methylpyrimidin-4-amine

HRID 475066
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HRID 475066 반응식
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH2:9])[CH:5]=2)[CH2:3][CH2:2]1.[Cl:10][C:11]1[N:16]=[C:15](Cl)[CH:14]=[C:13]([CH3:18])[N:12]=1.CCN(C(C)C)C(C)C.CCO>O>[Cl:10][C:11]1[N:16]=[C:15]([NH:9][C:6]2[CH:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[NH:8][N:7]=2)[CH:14]=[C:13]([CH3:18])[N:12]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 702EthanolHCID 794712,4-Dichloro-6-methylpyrimidineHCID 81531DiisopropylethylamineHCID 27580143-cyclopropyl-1H-pyrazol-5-amine

생성물 1

HCID 598196152-chloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)-6-methylpyrimidin-4-amine수율 59.1%

시약·촉매·용매 1

HCID 962
Water
용매

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온도
70 °C

실험 절차

A mixture of 5-cyclopropyl-1H-pyrazol-3-amine (1.98 g, 16.07 mmol), 2,4-dichloro-6-methyl-pyrimidine (2.62 g, 16.07 mmol), DIPEA (5.7 mL, 32.15 mmol) and anhydrous EtOH (50 mL) was stirred at 70° C. under N2 for 3 d. The reaction mixture was cooled and poured into water (ca. 700 mL). The reaction was stirred at RT overnight until solid precipitated out. The solid was filtered, washed with additional water and pumped dry under high-vacuum to afford 2.37 g (59%) of 189 as a solid: 1H NMR (400 MHz, DMSO-d6) δ 12.12 (s, 1H), 10.08 (s, 1H), 7.04 (br s, 1H), 5.93 (br s, 1H), 2.27 (s, 3H), 1.93 to 1.84 (m, 1H), 0.96-0.88 (m, 2H), 0.70-0.64 (m, 2H).

후처리

  1. temperatureThe reaction mixture was cooled
  2. stirringThe reaction was stirred at RT overnight until solid
  3. customprecipitated out
  4. filtrationThe solid was filtered
  5. washwashed with additional water
  6. custompumped dry under high-vacuum

출처 및 근거

ORD 기록
ord-bff638bb122c437bae93d31092009c21
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08637537B2

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