Triphenylphosphine → 2-[(E)-2-phenylethenyl]-6,7-dihydro-5H-pyrano[2,3-d]pyrimidine

HRID 657159Notes

Reaction equation

HRID 657159 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[C:6](=[O:19])[N:7]=[C:8](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:9][CH:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:13]1(/[CH:12]=[CH:11]/[C:8]2[N:9]=[CH:10][C:5]3[CH2:4][CH2:3][CH2:2][O:19][C:6]=3[N:7]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178517725HCID 178517725, compound

Product 1

HCID 684466292-[(E)-2-phenylethenyl]-6,7-dihydro-5H-pyrano[2,3-d]pyrimidineYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5-(3-hydroxypropyl)-2-[(E)-2-phenylethenyl]-4(1H)-pyrimidinone (1.0 g; 4.0 mmol) in THF (20 ml) was added triphenyl phosphine (1.6 g; 6.0 mmol) and diethyl azodicarboxylate (1.0 g; 6.0 mmol). The reaction was allowed to stir at room temperature under nitrogen for 14 hours. The reaction was partitioned between water (20 ml) and EtOAc (100 ml), and the aqueous phase was further extracted with EtOAc (2×50 ml). The combined organic extracts were dried with Na2SO4, the solvents were removed and the crude residue was purified by column chromatography on silica gel using a 0-2.5% MeOH in DCM gradient to provide the desired compound (0.81 g; 84%).

Workup

  1. customThe reaction was partitioned between water (20 ml) and EtOAc (100 ml)
  2. extractionthe aqueous phase was further extracted with EtOAc (2×50 ml)
  3. dry with materialThe combined organic extracts were dried with Na2SO4
  4. customthe solvents were removed
  5. customthe crude residue was purified by column chromatography on silica gel using a 0-2.5% MeOH in DCM gradient

Sources & evidence

ORD record
ord-c3ad91f280764620a49b2bb4d034d4e3
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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