Diisopropylethylamine → 1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine-8-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide
Reaction equation
[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[NH:8][C:7]([C:12]([OH:14])=O)=[N:6][C:5]=2[N:4]([CH3:15])[C:3]1=[O:16].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.Cl.[CH:52]([N:55]1[CH2:60][CH2:59][CH:58]([NH2:61])[CH2:57][CH2:56]1)([CH3:54])[CH3:53]>CN(C=O)C>[CH:52]([N:55]1[CH2:60][CH2:59][CH:58]([NH:61][C:12]([C:7]2[NH:8][C:9]3[C:10](=[O:11])[N:2]([CH3:1])[C:3](=[O:16])[N:4]([CH3:15])[C:5]=3[N:6]=2)=[O:14])[CH2:57][CH2:56]1)([CH3:54])[CH3:53]Participants
6
Reactant 4
HCID 81531Diisopropylethylamine2×
HCID 2252091,3-Dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1h-purine-8-carboxylic acid
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 177503401-(Propan-2-yl)piperidin-4-amine dihydrochlorideProduct 1
Reagents, catalysts & solvents 1
Procedure
100 mg (0.45 mmol) 1,3-Dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine-8-carboxylic acid were dissolved in 5 mL DMF. Subsequently 227 μl (1.35 mmol) DIPEA and 186.5 mg (0.495 mmol) HATU were added. After 1 h 105.6 mg (0.495 mmol) 1-isopropyl-piperidine-4-ylamine-dihydrochloride and 227 μl (1.35 mmol) DIPEA were added and the resulting mixture was stirred at room temperature for 4 h. The reaction mixture was concentrated and purified by preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid) to give 1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine-8-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide as its formiate.
Workup
- concentrationThe reaction mixture was concentrated
- custompurified by preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid)
Sources & evidence
- ORD record
- ord-4bc94180ce3c4bb5a7710b96f29abcea
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741341B2
Reaction notes
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