5-Amino-2-methoxyphenol → HCID 58928321、化合物

HRID 851911

反応式

HRID 851911 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 58928321HCID 58928321、化合物収率 69.9%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7e93572a87fb41efb1bbf94b4966e397
出典データセット
uspto-grants-2007_08
特許番号
US07253166B2

関連ノート

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