Ammonia → HCID 25133005、化合物

HRID 1042275

反応式

HRID 1042275 の反応式
F[C:2]1[C:7]([C:8]2[C:9]3[CH:16]=[CH:15][NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:17][C:18]1[C:19]([CH3:37])=[CH:20][CH:21]=[C:22]2[C:27]=1[N:26]=[CH:25][N:24]=[C:23]2[NH:28][C:29]1[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].N>C1COCC1.CO.CC(O)=O>[N:11]1[C:10]2[NH:14][CH:15]=[CH:16][C:9]=2[C:8]([C:7]2[C:2]([NH:17][C:18]3[C:19]([CH3:37])=[CH:20][CH:21]=[C:22]4[C:27]=3[N:26]=[CH:25][N:24]=[C:23]4[NH:28][C:29]3[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)=[N:13][CH:12]=1

参加物

8

反応物 4

HCID 222AmmoniaHCID 2733832Lithium HexamethyldisilazideHCID 596273704-(2-fluoropyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidineHCID 68725343HCID 68725343、化合物

生成物 1

HCID 25133005HCID 25133005、化合物

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
120 °C

実験手順

A mixture of 4-(2-fluoropyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidine (78 mg, 363 μmol) and 4-(8-amino-7-methylquinazolin-4-ylamino)benzonitrile (100 mg, 363 μmol) in THF (4 mL) was sonicated until all solids became a fine powder. Lithium bis(trimethylsilyl)amide (1.0 M solution in tetrahydrofuran; 1.64 mL, 1.64 mmol) was then added dropwise with stirring (all solids dissolved and then some solid appeared again). The mixture was stirred at rt for 10 min and then heated in a microwave at 120° C. for 30 min. The mixture was poured into MeOH (10 mL) and AcOH (0.5 mL) and stirred for 10 min, then 2 M NH3 in MeOH (20 mL) was added. Solvent was removed under vacuum and the residue was purified by flash chromatography eluting with MeOH(NH3)/DCM to give 4-(8-(3-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile. MS (ESI, pos. ion) m/z: 470.2 [M+H]+

後処理

  1. customwas sonicated until all solids
  2. dissolutiondissolved
  3. stirringThe mixture was stirred at rt for 10 min
  4. stirringstirred for 10 min
  5. customSolvent was removed under vacuum
  6. customthe residue was purified by flash chromatography
  7. washeluting with MeOH(NH3)/DCM

出典と根拠

ORDレコード
ord-6dea8a3f083f4893bea6ef05cc91325e
出典データセット
uspto-grants-2013_10
特許番号
US08557830B2

関連ノート

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