Triphenylphosphine → HCID 67367675, compound

HRID 1676226Notes

Reaction equation

HRID 1676226 reaction equation
[Cl:1][C:2]1[C:3]([OH:9])=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH:10]1([C:13]2[CH:14]=[N:15][C:16]([N:19]3[CH2:24][CH2:23][CH:22](O)[CH2:21][CH2:20]3)=[N:17][CH:18]=2)[CH2:12][CH2:11]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>CN(C=O)C.O>[Cl:1][C:2]1[C:3]([O:9][CH:22]2[CH2:23][CH2:24][N:19]([C:16]3[N:15]=[CH:14][C:13]([CH:10]4[CH2:12][CH2:11]4)=[CH:18][N:17]=3)[CH2:20][CH2:21]2)=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 54679224GimeracilHCID 58057790HCID 58057790, compound

Product 1

HCID 67367675HCID 67367675, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirring mixture of 5-chloro-4-hydroxypyridin-2(1H)-one (212 mg, 1.46 mmol), 1-(5-cyclopropylpyrimidin-2-yl)piperidin-4-ol (320 mg, 1.459 mmol, prepared according to procedures described in Example 173 Step A substituting 2-chloro-5-cyclopropylpyrimidine for 2-chloro-5-propylpyrimidine) and triphenylphosphine (574 mg, 2.19 mmol) in DMF (10 mL) at 0° C. was added diisopropyl azodicarboxylate (0.43 mL, 2.2 mmol). The reaction was stirred under Ar at room temperature for 2 days and then H2O was added. The resulting mixture was concentrated in vacuo to a yellow oil. The oil was purified by flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2 and then SiO2, 0 to 10% MeOH in CH2Cl2) to yield 153 mg of desired product as a white solid. MS (ESI) 347 (M+H).

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo to a yellow oil
  2. customThe oil was purified by flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2

Sources & evidence

ORD record
ord-6f5de83d813f4fbabf5c0f60172c222a
Source dataset
uspto-grants-2011_08
Patent number
US08003796B2

Reaction notes

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