1,2-Dichloroethane → 5-benzyl-2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine

HRID 1805868ノート

反応式

HRID 1805868 の反応式
[CH2:1]([N:8]1[C:16]2[C:15]([Cl:17])=[N:14][C:13](N)=[N:12][C:11]=2[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N(OC(C)(C)C)=O.[Cl:26]CCCl>>[CH2:1]([N:8]1[C:16]2[C:15]([Cl:17])=[N:14][C:13]([Cl:26])=[N:12][C:11]=2[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 111,2-DichloroethaneHCID 10906Tert-Butyl nitriteHCID 576936175-benzyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-2-amine

生成物 1

HCID 147277655-benzyl-2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine収率 77%

反応条件

温度
-10 °C

実験手順

To a suspension of 5-benzyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-2-amine (641 mg, 2.5 mmol) in 1,2-dichloroethane (35 mL) was cooled to −10° C. SbCl3 (850 mg, 3.7 mmol) was added. The reaction mixture was stirred for 5 min. t-butyl nitrite (2.1 mL, 17.4 mmol) was added dropwise and the stirred mixture was from −10° C. to room temperature for 5 h. Upon completion of the reaction, the reaction mixture was poured into ice water and washed with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography eluting with Hexanes:Ethyl acetate (9:1-1:1), and gave the product as an off-white solid (528 mg, 77%).

後処理

  1. additionwas added dropwise
  2. customUpon completion of the reaction
  3. washwashed with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel column chromatography
  9. washeluting with Hexanes:Ethyl acetate (9:1-1:1)

出典と根拠

ORDレコード
ord-9af5055370b14c76b7b05d544f9418a6
出典データセット
uspto-grants-2013_01
特許番号
US08354532B2

反応ノート

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