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

HRID 2189045Notes

Reaction equation

HRID 2189045 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-501478c812f4441ebeb49f011542bf1a
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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