Triphenylphosphine → Methyl 3-[5-(3-dimethylaminopropoxy)pyrimidin-2-yl]benzoate

HRID 1970877Notes

Reaction equation

HRID 1970877 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:37][N:38]([CH3:43])[CH2:39][CH2:40][CH2:41]O.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:37][N:38]([CH3:43])[CH2:39][CH2:40][CH2:41][O:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 766463-(Dimethylamino)-1-propanolHCID 59438048Methyl 3-(5-hydroxypyrimidin-2-yl)benzoate

Product 1

HCID 59484848Methyl 3-[5-(3-dimethylaminopropoxy)pyrimidin-2-yl]benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution, kept under nitrogen, of 6.1 g (26.5 mmol) of methyl 3-(5-hydroxypyrimidin-2-yl)benzoate, 10.5 g (39.8 mmol) of triphenylphosphine and 4.76 ml (39.8 mmol) of 3-(dimethylamino)-1-propanol in 200 ml of THF is cooled in an ice bath, and 8.21 ml (39.8 mmol) of diisopropyl azodicarboxylate are subsequently slowly added dropwise with stirring. After stirring at room temperature for 2 hours, the reaction mixture is evaporated in vacuo. The residue is partitioned between dichloromethane and saturated aqueous potassium hydrogensulfate solution. The aqueous phase is separated off, adjusted to a pH of 12 using saturated aqueous sodium hydroxide solution and extracted twice with dichloromethane. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent: methyl 3-[5-(3-dimethylaminopropoxy)pyrimidin-2-yl]benzoate as colourless crystals; m.p. 66° C.; ESI 316 (M+H); HPLC: 2.18 min (method B).

Workup

  1. temperatureis cooled in an ice bath
  2. stirringAfter stirring at room temperature for 2 hours
  3. customthe reaction mixture is evaporated in vacuo
  4. customThe residue is partitioned between dichloromethane and saturated aqueous potassium hydrogensulfate solution
  5. customThe aqueous phase is separated off
  6. extractionextracted twice with dichloromethane
  7. dry with materialThe organic phase is dried over sodium sulfate
  8. customevaporated
  9. customThe residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent
  10. custom2.18 min (method B)

Sources & evidence

ORD record
ord-f11e9fe7c902404785c35fd5a6705327
Source dataset
uspto-grants-2013_04
Patent number
US08431572B2

Reaction notes

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