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Hydrochloric Acid → 5-Bromo-4-chloro-6-phenylfuro[2,3-d]pyrimidine

HRID 1926887
ノート
印刷プレビュー

反応式

HRID 1926887 の反応式
[Br:1][C:2]1[C:10]2[C:9](N)=[N:8][CH:7]=[N:6][C:5]=2[O:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[ClH:18].O1CCOCC1.N(OCCC(C)C)=O>C(Cl)(Cl)Cl.O>[Br:1][C:2]1[C:10]2[C:9]([Cl:18])=[N:8][CH:7]=[N:6][C:5]=2[O:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 312751,4-DioxaneHCID 594278295-Bromo-6-phenylfuro[2,3-d]pyrimidine-4-amine

生成物 1

HCID 580168535-Bromo-4-chloro-6-phenylfuro[2,3-d]pyrimidine収率 55.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6212Chloroform溶媒

実験手順

Put 54 g (186 mmol) 5-bromo-6-phenylfuro[2,3-d]pyrimidine-4-amine in 135 ml chloroform, add 70 ml 4 N hydrogen chloride in dioxan (280 mmol) and heat to reflux. Add 50 ml (372 mmol) isoamyl nitrite dropwise (evolution of gas). At the end of addition, stir for 3 h under reflux, before adding the cooled reaction mixture to water and extracting it with dichloromethane. Wash the organic phase with satd. sodium hydrogencarbonate solution, dry over sodium sulphate and concentrate by vacuum evaporation. Purify the raw product by chromatography on silica gel (eluent: dichloromethane). For further purification, mix the product in methanol, filter with suction, and dry at high vacuum. 32 g of the target product (55.5% of theor.) is obtained.

後処理

  1. temperatureheat to reflux
  2. additionAt the end of addition
  3. temperatureunder reflux
  4. additionbefore adding
  5. extractionextracting it with dichloromethane
  6. washWash the organic phase with satd
  7. dry with materialsodium hydrogencarbonate solution, dry over sodium sulphate
  8. concentrationconcentrate by vacuum evaporation
  9. customPurify the raw product by chromatography on silica gel (eluent: dichloromethane)
  10. customFor further purification
  11. additionmix the product in methanol
  12. filtrationfilter with suction
  13. customdry at high vacuum

出典と根拠

ORDレコード
ord-14799d726ff64c7a8766f61a4e938816
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08183246B2

反応ノート

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