Iodine → 6-iodo-4-methoxy-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine

HRID 854383ノート

反応式

HRID 854383 の反応式
[CH3:1][O:2][C:3]1[C:4]2[CH:11]=[CH:10][N:9]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]=2[N:6]=[CH:7][N:8]=1.C([Li])CCC.[I:27]I>O1CCCC1.CCCCCC>[I:27][C:10]1[N:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:13])=[O:14])[C:5]2[N:6]=[CH:7][N:8]=[C:3]([O:2][CH3:1])[C:4]=2[CH:11]=1

参加物

6

反応物 3

HCID 807IodineHCID 694318294-Methoxy-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidineHCID 178418339Butyllithium

生成物 1

HCID 694318556-iodo-4-methoxy-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine収率 83.7%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-70 °C

実験手順

To a solution of 4-methoxy-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine [2.23 g, Reference Example 7] in tetrahydrofuran (35 mL) at −78° C. was added drop wise a solution of butyl lithium in hexane (5 mL, 1.6M) under inert atmosphere. The solution was stirred at −70° C. for 1 hour and iodine (2.05 g) was added. The reaction mixture was stirred at −70° C. for another 1 hour, allowed to reach room temperature and partitioned between ethyl acetate and aqueous sodium sulfite solution. The organic phase was separated, then dried over magnesium sulfate and then evaporated under reduced pressure to give the title compound (2.64 g) as an amorphous solid. MS: 430 [MH]+. LCMS (Method B) RT=4.15 minutes.

後処理

  1. stirringThe reaction mixture was stirred at −70° C. for another 1 hour
  2. customto reach room temperature
  3. custompartitioned between ethyl acetate and aqueous sodium sulfite solution
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-770c36d41e3b451393dbb301fe610ee0
出典データセット
uspto-grants-2007_08
特許番号
US07259154B2

反応ノート

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