Water → HCID 68964849, compound

HRID 226417Notes

Reaction equation

HRID 226417 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[CH:6][N:5]=[C:4](SC)[N:3]=1.[CH2:20]([N:27]1[CH2:31][CH2:30][CH:29]([NH2:32])[CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCOC(C)=O.O>O1CCOCC1>[CH2:20]([N:27]1[CH2:31][CH2:30][CH:29]([NH:32][C:4]2[N:3]=[C:2]([CH3:1])[C:7]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])=[CH:6][N:5]=2)[CH2:28]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 27566131-Benzyl-3-aminopyrrolidineHCID 68967730HCID 68967730, compound

Product 1

HCID 68964849HCID 68964849, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of benzyl 4-methyl-2-(methylthio)-5-pyrimidinecarboxylate (6.0 g) and 1-benzyl-3-aminopyrrolidine (5.78 g) in dioxane (10 ml) was stirred at 130° C. for 15 hours under atmospheric pressure of nitrogen. The reaction mixture was poured into a mixture of AcOEt and H2O and the organic layer was washed with brine and dried over MgSO4. The solvent was evaporated in vacuo and the residue was chromatographed on allunima eluting with AcOEt-n-hexane (6:4). The eluted fractions containing the desired product were collected and evaporated in vacuo to give benzyl 2-[(1-benzyl-3-pyrrolidinyl]amino)-4-methyl-5-pyrimidinecarboxylate (3.06 g).

Workup

  1. washthe organic layer was washed with brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was chromatographed on allunima eluting with AcOEt-n-hexane (6:4)
  5. additionThe eluted fractions containing the desired product
  6. customwere collected
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-4318dacb2a51415689fcec9232187ea4
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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