Triphenylphosphine → Methyl 3-[5-(2-morpholin-4-ylethoxy)pyrimidin-2-yl]benzoate

HRID 330798Notes

Reaction equation

HRID 330798 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.[N:37]1([CH2:43][CH2:44]O)[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[N:37]1([CH2:43][CH2:44][O:1][C:2]2[CH:7]=[N:6][C:5]([C:8]3[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=3)[C:11]([O:13][CH3:14])=[O:12])=[N:4][CH:3]=2)[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 59438048Methyl 3-(5-hydroxypyrimidin-2-yl)benzoate

Product 1

HCID 58496335Methyl 3-[5-(2-morpholin-4-ylethoxy)pyrimidin-2-yl]benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution, kept under nitrogen, of 10.1 g (44 mmol) of methyl 3-(5-hydroxypyrimidin-2-yl)benzoate, 17.3 g (66 mmol) of triphenylphosphine and 5.9 ml (48.4 mmol) of 2-morpholin-4-ylethanol in 100 ml of THF is cooled in an ice bath, and 12.95 ml (66 mmol) of diisopropyl azodicarboxylate are slowly added dropwise with stirring. After stirring at room temperature for 2 hours, the reaction mixture is evaporated in vacuo. The residue is taken up in 100 ml of dichloromethane and 100 ml of water. The organic phase is dried over sodium sulfate and evaporated. The residue is recrystallised from isopropanol: methyl 3-[5-(2-morpholin-4-ylethoxy)pyrimidin-2-yl]benzoate as beige crystals; m.p. 89-91°; ESI 344 (M+H); HPLC: 2.06 min (method A).

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. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated
  6. customThe residue is recrystallised from isopropanol
  7. custom2.06 min (method A)

Sources & evidence

ORD record
ord-2531ced09c7a48d68c3f865d1b3e3d1c
Source dataset
uspto-grants-2014_11
Patent number
US08877751B2

Reaction notes

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