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

HRID 1926887
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HRID 1926887 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매
HCID 6212Chloroform용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-14799d726ff64c7a8766f61a4e938816
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08183246B2

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