Triphenylphosphine → 9-(3-cyclopropyl-propoxy)-2-((S)-1-[1,4]dioxan-2-ylmethoxy)-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one
Reaction equation
[O:1]1[CH2:6][CH2:5][O:4][CH2:3][C@H:2]1[CH2:7][O:8][C:9]1[CH:23]=[C:13]2[C:14]3[C:19]([CH2:20][CH2:21][N:12]2[C:11](=[O:24])[N:10]=1)=[CH:18][C:17]([OH:22])=[CH:16][CH:15]=3.C[C:26]([CH3:32])([CH3:31])[CH2:27][CH2:28][CH2:29]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCOCC1>[CH:26]1([CH2:27][CH2:28][CH2:29][O:22][C:17]2[CH:18]=[C:19]3[C:14](=[CH:15][CH:16]=2)[C:13]2=[CH:23][C:9]([O:8][CH2:7][C@@H:2]4[CH2:3][O:4][CH2:5][CH2:6][O:1]4)=[N:10][C:11](=[O:24])[N:12]2[CH2:21][CH2:20]3)[CH2:31][CH2:32]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Intermediate 6 (2.12 g, 2.42 mmol, 1 eq.), 4,4-dimethyl-pentan-1-ol (0.77 g, 7.71 mmol, 1.2 eq.) and PPh3 (2.02 g, 7.71 mmol, 1.2 eq.) were suspended in 1,4-dioxane (50 mL) and the mixture was degassed with N2. DIAD (1.56 mL, 7.71 mmol, 1.1 eq.) was added dropwise and the reaction was stirred at RT for 2 h. The reaction mixture was quenched with brine and extracted with EtOAc, the organic phase was dried over MgSO4 and evaporated to dryness. Compound 143 was obtained by purification by flash chromatography on silica gel, eluting from 60 to 100% EtOAc/H.
Workup
- customthe mixture was degassed with N2
- customThe reaction mixture was quenched with brine
- extractionextracted with EtOAc
- dry with materialthe organic phase was dried over MgSO4
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-e679162b4c9945d9aea37e0913b2ad19
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09255095B2
Reaction notes
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