Formaldehyde → 4-(2-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)morpholine
Reaction equation
F[C:2](F)(F)C(O)=O.[Cl:8][C:9]1[N:10]=[C:11]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:12]2[CH2:17][NH:16][CH2:15][C:13]=2[N:14]=1.C=O.CCN(CC)CC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>CN(C=O)C>[Cl:8][C:9]1[N:10]=[C:11]([N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[C:12]2[CH2:17][N:16]([CH3:2])[CH2:15][C:13]=2[N:14]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
To a stirring solution of 4-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)morpholine trifluoroacetate (intermediate 20) (2.16 g, 2.0 mmol) in DMF, was added aqueous formaldehyde (0.3 ml, 4.0 mmol) and Et3N (560 uL, 4.0 mmol). The reaction mixture was stirred at room temperature (20° C.) for 45 minutes, before adding sodium triacetoxy borohydride (848 mg, 4.0 mmol). The reaction mixture was then stirred over-night at room temperature (20° C.). The reaction mixture was basified (with 2M NaOH) before partitioning between water (25 ml) and DCM (50 ml). The organic layer was recovered, passed through a hydrophobic frit and the solvent removed in vacuo, affording the title compound as a pink solid, which was used without further purification.
Workup
- stirringThe reaction mixture was then stirred over-night at room temperature (20° C.)
- custombefore partitioning between water (25 ml) and DCM (50 ml)
- customThe organic layer was recovered
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-128115282e174041af7f0a16ee17665d
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785457B2
Reaction notes
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