Acetic Acid → 4-(2-Chloro-9-methyl-8-((4-(methylsulfonyl)piperazin-1-yl)methyl)-9H-purin-6-yl)morpholine
Reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:12]=O)[N:8]2[CH3:11])=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:3]=1.[CH3:20][S:21]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)(=[O:23])=[O:22].COC(OC)OC.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:12][N:27]3[CH2:28][CH2:29][N:24]([S:21]([CH3:20])(=[O:23])=[O:22])[CH2:25][CH2:26]3)[N:8]2[CH3:11])=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:3]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Chloro-9-methyl-6-morpholino-9H-purine-8-carbaldehyde was treated with 1.1 eq 1-(methylsulfonyl)piperazine, 7 eq trimethylorthoformate, 1 eq of acetic acid in 2 mL of dichloroethane for 6 hours upon which 1.1 eq of sodium triacetoxyborohydride was added to the reaction mixture. The reaction mixture was extracted with dichloromethane and water to give crude intermediate 4-(2-chloro-9-methyl-8-((4 (methylsulfonyl)piperazin-1-yl)methyl)-9H-purin-6-yl)morpholine which was then reacted with 1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole via General Procedure A and purified via reverse phase HPLC to give 41.8 mg 138 as a white solid. MS (Q1) 512.2 (M)+.
Workup
- additionwas added to the reaction mixture
- extractionThe reaction mixture was extracted with dichloromethane and water
Sources & evidence
- ORD record
- ord-91bf1a31a29844ce8876b8f07a94518d
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158624B2
Reaction notes
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