Iodine → 2-Iodo-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-one
Reaction equation
N[C:2]1[N:3]([CH2:28][CH2:29][CH3:30])[C:4](=[O:27])[C:5]2[NH:6][C:7]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=4)[CH:15]=3)=[N:8][C:9]=2[N:10]=1.N(OCCC(C)C)=O.[I:39]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>C1COCC1>[I:39][C:2]1[N:3]([CH2:28][CH2:29][CH3:30])[C:4](=[O:27])[C:5]2[NH:6][C:7]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:25])([F:24])[F:26])[CH:18]=4)[CH:15]=3)=[N:8][C:9]=2[N:10]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 2-Amino-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-one (prepared as given in Example 13) (0.169 g, 0.41 mmol), isoamyl nitrite (0.2 ml, 1.5 mmol), iodine (83 mg, 0.32 mmol) was taken in THF (5 ml) and stirred for 2 hours at 80° C. Reaction mixture was cooled and saturated solution of Na2S2O3 was added and extracted with ethyl acetate (3×5 ml). The organic layer was washed with brine (10 ml), dried over Na2SO4 and evaporated to obtain 2-Iodo-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-one (93 mg, 44%).
Workup
- customReaction mixture
- temperaturewas cooled
- extractionextracted with ethyl acetate (3×5 ml)
- washThe organic layer was washed with brine (10 ml)
- dry with materialdried over Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-3db922ab793b4538b84133dbd61bcfcf
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09284316B2
Reaction notes
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