Ammonia → 5-(4-amino-3-methoxyphenyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 251491Notes

Reaction equation

HRID 251491 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:17]=[CH:16][C:14]([NH2:15])=[C:13]([O:18][CH3:19])[CH:12]=3)=[CH:9][N:8]([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[NH3:25]>O1CCOCC1>[NH2:15][C:14]1[CH:16]=[CH:17][C:11]([C:10]2[C:3]3[C:2]([NH2:25])=[N:7][CH:6]=[N:5][C:4]=3[N:8]([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:9]=2)=[CH:12][C:13]=1[O:18][CH3:19]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 541919345-(4-Amino-3-methoxyphenyl)-4-chloro-7-cyclopentylpyrrolo[2,3-d]pyrimidine

Product 1

HCID 539252325-(4-amino-3-methoxyphenyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-(4-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyaniline (0.45 g, 1.31 mmol), ammonia (115 ml, SG 0.88) and 1,4-dioxane (115 ml) was heated and stirred at 120° C. in a pressure vessel overnight. The mixture was allowed to cool to ambient temperature and the solvent was removed under reduced pressure to give a residue which was partitioned between water and ethyl acetate. The organic layer was separated and the aqueous layer was further extracted with ethyl acetate twice. The combined ethyl acetate extracts were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and evaporated to give 5-(4-amino-3-methoxyphenyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine as brown solids (0.32 g, 0.99 mmol): 1H NMR (DMSO-d6, 400 MHz) δ 8.09 (s, 1H), 7.24 (s, 1H), 6.88 (d, 1H), 6.79 (dd, 1H), 6.71 (d, 1H), 6.01 (broad, 2H), 5.06 (m, 1H), 4.79 (broad, 2H), 3.81 (s, 3H), 2.10 (m, 2H), 1.87-1.92 (m, 4H), 1.68 (m, 2H); MH+324.

Workup

  1. temperaturewas heated
  2. temperatureto cool to ambient temperature
  3. customthe solvent was removed under reduced pressure
  4. customto give a residue which
  5. customwas partitioned between water and ethyl acetate
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was further extracted with ethyl acetate twice
  8. washThe combined ethyl acetate extracts were washed with saturated aqueous sodium chloride solution
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-4574ee8124d644ed938bc14fee2f1dd4
Source dataset
uspto-grants-2011_01
Patent number
US07863444B2

Reaction notes

Loading…