Potassium Carbonate → 7-isopropyl-5-[4-(2-nitrophenoxy)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine
Reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:18]([CH3:20])[CH3:19])[C:4]=2[N:5]=[CH:6][N:7]=1.F[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N+:28]([O-:30])=[O:29].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:18]([N:8]1[C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=2[C:10]([C:11]2[CH:12]=[CH:13][C:14]([O:17][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N+:28]([O-:30])=[O:29])=[CH:15][CH:16]=2)=[CH:9]1)([CH3:20])[CH3:19]Participants
5
Conditions
- Temperature
- 120 °C
Procedure
A mixture of 4-amino-5-(4-hydroxyphenyl)-7-isopropylpyrrolo[2,3-d]-pyrimidine (0.29 g), 2-fluoronitrobenzene (0.15 g), potassium carbonate (0.149 g) and N,N-dimethylformamide (4.0 ml) was shaken and heated at 120° C. for 5 hours. The mixture was evaporated to dryness under reduced pressure and the residue was partitioned between ethyl acetate (30 ml) and water (20 ml). The organic layer was separated, washed with water, and then with dilute sodium hydroxide solution, and then with brine, then dried, filtered and evaporated to give a solid which was triturated with ether to give 7-isopropyl-5-[4-(2-nitrophenoxy)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine. The structure was confirmed by 1H nmr.
Workup
- customThe mixture was evaporated to dryness under reduced pressure
- customthe residue was partitioned between ethyl acetate (30 ml) and water (20 ml)
- customThe organic layer was separated
- washwashed with water
- dry with materialwith dilute sodium hydroxide solution, and then with brine, then dried
- filtrationfiltered
- customevaporated
- customto give a solid which
- customwas triturated with ether
Sources & evidence
- ORD record
- ord-73a0ae6ddff841c5803c86df9a19e173
- Source dataset
- uspto-grants-1999_12
- Patent number
- US06001839
Reaction notes
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