Tetrabutylammonium Fluoride → HCID 58777630、化合物

HRID 1371735ノート

反応式

HRID 1371735 の反応式
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([F:16])=[C:14]([F:17])[CH:13]=[C:12]([O:18][Si](C(C)(C)C)(C)C)[C:11]=2[O:26][CH3:27])=[O:9])=[CH:6][N:5]=[C:4]([NH:28][CH:29]2[CH2:34][CH2:33][N:32]([S:35]([CH3:38])(=[O:37])=[O:36])[CH2:31][CH2:30]2)[N:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:11]([O:26][CH3:27])=[C:12]([OH:18])[CH:13]=[C:14]([F:17])[C:15]=2[F:16])=[O:9])=[CH:6][N:5]=[C:4]([NH:28][CH:29]2[CH2:30][CH2:31][N:32]([S:35]([CH3:38])(=[O:36])=[O:37])[CH2:33][CH2:34]2)[N:3]=1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 58777580HCID 58777580、化合物

生成物 1

HCID 58777630HCID 58777630、化合物収率 58.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of [4-amino-2-(1-methanesulfonyl-piperidin-4-ylamino)-pyrimidin-5-yl]-[3-(tert-butyl-dimethyl-silanyloxy)-5,6-difluoro-2-methoxy-phenyl]-methanone (675 mg, 1.181 mmol, Example 270) in tetrahydrofuran (10 mL) was added tetrabutylammonium fluoride (1.240 mL, 1.24 mmol, 1 M solution in tetrahydrofuran, Aldrich). The mixture was stirred at room temperature for 15 minutes and then concentrated to dryness. The residue was taken up in methylene chloride and washed with saturated solution of sodium bicarbonate. The organic layer was dried over anhydrous magnesium sulfate. The solids were filtered off and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, 60 Å silica gel, eluting with 65–80% ethyl acetate in hexanes then 5% methanol in ethyl acetate) yielded [4-amino-2-(1-methanesulfonyl-piperidin-4-ylamino)-pyrimidin-5-yl]-(2,3-difluoro-5-hydroxy-6-methoxy-phenyl)-methanone as white solids (315 mg, 58%). HR-MS (ES, m/z) calculated for C18H22N5O5SF2 [(M+H)+] 458.1308, observed 458.1304.

後処理

  1. concentrationconcentrated to dryness
  2. washwashed with saturated solution of sodium bicarbonate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationThe solids were filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. customPurification of the crude residue by flash chromatography (Biotage system, 60 Å silica gel
  7. washeluting with 65–80% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-771e8d52dac54b74a6770cc7a95b53c5
出典データセット
uspto-grants-2007_01
特許番号
US07157455B2

反応ノート

読み込み中…