alpha-Bromo-o-fluorotoluene → 2-[[2-amino-5-[[(2-fluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-(2R)-1-propanol

HRID 1006512ノート

反応式

HRID 1006512 の反応式
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[NH2:10][C:11]1[S:12][C:13]2[C:18]([NH:19][C@H:20]([CH3:23])[CH2:21][OH:22])=[N:17][C:16]([SH:24])=[N:15][C:14]=2[N:25]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.CN1CCCC1=O>[NH2:10][C:11]1[S:12][C:13]2[C:18]([NH:19][C@H:20]([CH3:23])[CH2:21][OH:22])=[N:17][C:16]([S:24][CH2:4][C:3]3[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=3[F:1])=[N:15][C:14]=2[N:25]=1

参加物

5

反応物 3

HCID 67968alpha-Bromo-o-fluorotolueneHCID 81531DiisopropylethylamineHCID 178461804HCID 178461804、化合物

生成物 1

HCID 235198222-[[2-amino-5-[[(2-fluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-(2R)-1-propanol収率 35%

試薬・触媒・溶媒 1

HCID 18784345DMSO N-methylpyrrolidinone溶媒

実験手順

2-fluorobenzylbromide (0.369 g) was added portionwise to a solution of the product of example 32 step b) (0.5 g) and diisopropylethylamine (0.26 g) in DMSO/N-methylpyrrolidinone (4 ml/0.5 ml) at 50° C. and stirring maintained for 1 h. The mixture was partitioned between H2O (200 ml) and EtOAc (120 ml). The organics were recovered and washed flier with H2O (200 ml), dried over MgSO4 and concentrated onto silica gel. The subtitle compound was purified by flash chromatography using DCM then EtOAc as eluents to yield a white solid (245 mg, 35%).

後処理

  1. temperaturemaintained for 1 h
  2. customThe mixture was partitioned between H2O (200 ml) and EtOAc (120 ml)
  3. customThe organics were recovered
  4. washwashed flier with H2O (200 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated onto silica gel
  7. customThe subtitle compound was purified by flash chromatography

出典と根拠

ORDレコード
ord-bcd0ebf3d84c48b8862abb3994de21c2
出典データセット
uspto-grants-2004_09
特許番号
US06790850B1

反応ノート

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