5-Amino-2-methoxyphenol → HCID 58928321, 화합물

HRID 851911

반응식

HRID 851911 반응식
[Br:1][C:2]1[NH:11][C:5]2[N:6]=[CH:7][N:8]=[C:9](Cl)[C:4]=2[CH:3]=1.[OH:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[NH2:16].C(N(C(C)C)CC)(C)C>C(O)CCC>[Br:1][C:2]1[NH:11][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:16][C:15]3[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:13]([OH:12])[CH:14]=3)[C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 743145-Amino-2-methoxyphenolHCID 81531DiisopropylethylamineHCID 457898276-Bromo-4-chloro-7H-pyrrolo[2,3-D]pyrimidine

생성물 1

HCID 58928321HCID 58928321, 화합물수율 69.9%

시약·촉매·용매 1

HCID 2631-Butanol용매

반응 조건

온도
120 °C

실험 절차

6-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (100 mg, 0.41 mmol), prepared as in reference 1, is mixed with 3-hydroxy-4-methoxyaniline (170 mg, 1.22 mmol) and diisopropylethylamine (213 μL, 1.22 mmol) in n-butanol (1.3 mL). The mixture is heated to 120° C. for 18 hours, with stirring. The reaction is then cooled to ambient temperature and the solvent is removed. The resultant crude product is purified by flash column chromatography using a gradient of 3-5% MeOH in DCM to yield 5-(6-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-2-methoxy-phenol (96 mg; 66%); 1H NMR (500 MHz, d-methanol) δ 8.17 (s, 1H), 7.16 (s, 1H), 6.98 (d, J=8.6 Hz, 1H), 6.92 (d, J=8.6 Hz, 1H), 6.61 (s, 1H), 3.87 (s, 3H), 3.75 (s, 3H); LC-ESMS observed [M+H]+ 349.0 (calculated for C14H13BrN4O2, 348.0).

후처리

  1. temperatureThe reaction is then cooled to ambient temperature
  2. customthe solvent is removed
  3. customThe resultant crude product is purified by flash column chromatography

출처 및 근거

ORD 기록
ord-7e93572a87fb41efb1bbf94b4966e397
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253166B2

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