Diisopropylamine → 1,3-Dimethyl-2,4-dioxo-6-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-ylboronic acid
Reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][N:14]1[C:19]2=[CH:20][N:21]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:22]=[C:18]2[C:17](=[O:31])[N:16]([CH3:32])[C:15]1=[O:33].C([O:37][B:38](OC(C)C)[O:39]C(C)C)(C)C>C1COCC1>[CH3:13][N:14]1[C:19]2=[CH:20][N:21]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:28])([CH3:30])[CH3:29])[C:22]([B:38]([OH:39])[OH:37])=[C:18]2[C:17](=[O:31])[N:16]([CH3:32])[C:15]1=[O:33]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -5 °C
Procedure
Butyl lithium (1.26M, 28.4 mL, 35.8 mmol) was added dropwise to a solution of diisopropylamine (3.63 g, 35.8 mmol) in THF (20 mL) at −78° C., keeping the internal temperature below −40° C. Once the addition was complete, the contents of the flask were allowed to warm to −5° C., then were re-cooled to −78° C. The resulting mixture was cannulated over a period of about 30 minutes into a suspension of 1,3-dimethyl-6-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (step 1) (6.93 g, 22.4 mmol) in THF (75 mL) at −78° C. The mixture was stirred at −78° C. for 30 minutes, then triisopropylborate (8.3 mL, 35.8 mmol) was added dropwise. The solution was stirred at −78° C. for 1.5 hours, then was quenched by carefully adding sat ammonium chloride (200 mL).
Workup
- customthe internal temperature below −40° C
- additionOnce the addition
- temperaturewere re-cooled to −78° C
- stirringThe solution was stirred at −78° C. for 1.5 hours
- customwas quenched
- additionby carefully adding
Sources & evidence
- ORD record
- ord-548ec66e70e848969509b85c99e2e5cb
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09359381B2
Reaction notes
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