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

HRID 655331Notes

Reaction equation

HRID 655331 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-fc386502d7ef4f94a752e03761ee1abf
Source dataset
uspto-grants-2011_12
Patent number
US08071593B2

Reaction notes

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