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Triphenylphosphine → 9-(3-cyclopropyl-propoxy)-2-((S)-1-[1,4]dioxan-2-ylmethoxy)-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one

HRID 1773297
Notes
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Reaction equation

HRID 1773297 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]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 183934,4-Dimethyl-1-pentanolHCID 5363146Diisopropyl azodicarboxylateHCID 136409086(S)-2-((1,4-dioxan-2-yl)methoxy)-9-hydroxy-6,7-dihydro-4H-pyrimido[6,1-a]isoquinolin-4-one

Product 1

HCID 866884619-(3-cyclopropyl-propoxy)-2-((S)-1-[1,4]dioxan-2-ylmethoxy)-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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

  1. customthe mixture was degassed with N2
  2. customThe reaction mixture was quenched with brine
  3. extractionextracted with EtOAc
  4. dry with materialthe organic phase was dried over MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-e679162b4c9945d9aea37e0913b2ad19
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09255095B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes