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Sodium hydride → 7-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-3-(2,2,2-trifluoroethyl)pyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione

HRID 510145
ノート
印刷プレビュー

反応式

HRID 510145 の反応式
[NH2:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[O:9])=[CH:6][N:5]=[C:4]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[N:17]=2)[N:3]=1.[H-].[Na+].[C:35](N1C=CN=C1)(N1C=CN=C1)=[O:36]>C1COCC1>[F:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][N:18]1[C:19]2=[N:20][CH:21]=[CH:22][CH:23]=[C:24]2[C:16]([C:4]2[N:3]=[C:2]3[NH:1][C:35](=[O:36])[N:10]([CH2:11][C:12]([F:13])([F:14])[F:15])[C:8](=[O:9])[C:7]3=[CH:6][N:5]=2)=[N:17]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 666142844-Amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-N-(2,2,2-trifluoroethyl)pyrimidine-5-carboxamide

生成物 1

HCID 666349057-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-3-(2,2,2-trifluoroethyl)pyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

50 mg (0.11 mmol) of 4-amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-N-(2,2,2-trifluoroethyl)pyrimidine-5-carboxamide (example 103A) were initially charged in 5 ml of THF and, while cooling with ice, 18.0 mg (0.45 mmol) of sodium hydride (60% in mineral oil) were added over a period of 5 min. The mixture was stirred for 25 min, then 27.3 mg (0.17 mmol) of 1,1′-carbonyldiimidazole were added with ice cooling over 5 min. Conversion was effected at room temperature for 1 h and at reflux temperature for 90 min. After cooling, the mixture was hydrolyzed and then the organic phase was diluted with 10 ml of THF. After drying with sodium sulfate, the volatile components were removed by means of a rotary evaporator. Then the crude material was purified by means of preparative HPLC [column: Reprosil C18, 10 μm, 250*30 mm; flow rate: 40 ml/min; eluent: methanol/0.05% formic acid; gradient: 50% methanol→95% methanol)]. The volatile components of the product fractions were removed on the rotary evaporator. Thus, 26 mg (48% of theory) of the target compound were obtained.

後処理

  1. additionwere added over a period of 5 min
  2. waitConversion was effected at room temperature for 1 h
  3. temperatureat reflux temperature for 90 min
  4. temperatureAfter cooling
  5. dry with materialAfter drying with sodium sulfate
  6. customthe volatile components were removed by means of a rotary evaporator
  7. customThen the crude material was purified by means of preparative HPLC [column
  8. customThe volatile components of the product fractions were removed on the rotary evaporator
  9. customThus, 26 mg (48% of theory) of the target compound were obtained

出典と根拠

ORDレコード
ord-0432f6b453ae43c7ba1c482993ce1091
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09096592B2

反応ノート

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