Methyl iodide → 2-Chloro-9-methyl-6-(4-morpholinyl)-9H-purine
Reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[N:3]=1.[CH3:17]I>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:17])=[C:4]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[N:3]=1Participants
3
Procedure
4-(2-Chloro-9H-purin-6-yl)morpholine (510 mg) was reacted with methyl iodide via General Procedure C to give 4-(2-chloro-9-methyl-9H-purin-6-yl)morpholine. 4-(2-Chloro-9-methyl-9H-purin-6-yl)morpholine (100 mg) was cooled in 1.5 mL of anhydrous THF to −78° C. before adding 2 eq of a 2.5 M solution of n-butyl lithium. The reaction was stirred for 1 hour at −78° C. upon which 3 eq of DMF were added. The reaction was subsequently warmed to 0° C. after 30 minutes. The reaction was quenched into a cold 0.25 M aqueous solution of HCl and the orange solid was filtered, collected and dried to give 48 mg crude intermediate 2-chloro-9-methyl-6-morpholino-9H-purine-8-carbaldehyde.
Sources & evidence
- ORD record
- ord-0b54810c235f4ef5a43c5577d652f1e3
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445487B2
Reaction notes
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