Triphenylphosphine → HCID 178518545, compound

HRID 474810Notes

Reaction equation

HRID 474810 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][S:16][C:17]3[NH:18][CH:19]=[C:20]([CH2:24]O)[C:21](=[O:23])[N:22]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:26]([F:29])([F:28])[F:27].CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:63]1[CH2:67][CH2:66][CH2:65][CH2:64]1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:15][S:16][C:17]3[NH:18][CH:19]=[C:20]([CH2:24][N:63]4[CH2:67][CH2:66][CH2:65][CH2:64]4)[C:21](=[O:23])[N:22]=3)=[CH:13][CH:14]=2)=[CH:4][C:3]=1[C:26]([F:29])([F:28])[F:27]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 31268PyrrolidineHCID 5363146Diisopropyl azodicarboxylateHCID 178518547HCID 178518547, compound

Product 1

HCID 178518545HCID 178518545, compoundYield 13.48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The same procedure as E69 from 2-{[(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)methyl]thio}-5-(hydroxymethyl)-4(1H)-pyrimidinone (53 mg, 0.120 mmol), DIAD (0.035 mL, 0.180 mmol), triphenylphosphine (47.1 mg, 0.180 mmol) and pyrrolidine (25.5 mg, 0.359 mmol) in DMF (2 mL), except that the temperature was up to 50° C., to afford the title compound (8 mg, 13.48% yield). LCMS: rt=3.06 min, [M+H+]=496

Workup

  1. customwas up to 50° C.

Sources & evidence

ORD record
ord-64f0d8ff261d4800b9d46a0abed20df7
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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