Hydrochloric Acid → (4-Isopropoxy-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-2-yl)-amine

HRID 1966397Notes

Reaction equation

HRID 1966397 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[CH:11]([O:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1)([CH3:13])[CH3:12].Cl>C(O)CCC>[CH:11]([O:14][C:15]1[CH:21]=[CH:20][C:18]([NH:19][C:2]2[N:3]=[CH:4][C:5]3[CH:10]=[CH:9][NH:8][C:6]=3[N:7]=2)=[CH:17][CH:16]=1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 821124-IsopropoxyanilineHCID 57067742-Chloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 68639256(4-Isopropoxy-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-2-yl)-amine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
140 °C

Procedure

To a suspension of 2-chloro-7H-pyrrolo[2,3-d]pyrimidine (700 mg, 4.33 mmol) in BuOH (10 mL) is added 4-isopropoxyaniline (1.31 g, 8.66 mmol) and concentrated aqueous HCl (37%, 1.28 mL, 13.0 mmol). The reaction mixture is heated to 140° C. for 24 h, cooled to rt, and concentrated under reduce pressure. The residue is dissolved in EtOAc and the organic layer is washed with saturated aqueous Na2CO3 solution (2×). The organic layer is dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue solid residue is triturated with hexane to yield the title compound as an off-white solid.

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in EtOAc
  4. washthe organic layer is washed with saturated aqueous Na2CO3 solution (2×)
  5. dry with materialThe organic layer is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue solid residue is triturated with hexane

Sources & evidence

ORD record
ord-7b1b1fe4ef4f428883eb08f2c2b1aec8
Source dataset
uspto-grants-2013_04
Patent number
US08420657B2

Reaction notes

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