N-(4-Bromobutyl)phthalimide → 4-Amino-2-(4-phthalimidobutylthio)pyrimidine

HRID 34778

Reaction equation

HRID 34778 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[S:3].N12CCCCC1C=NCCC2.Br[CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35]>C(O)C>[NH2:6][C:5]1[CH:7]=[CH:8][N:1]=[C:2]([S:3][CH2:21][CH2:22][CH2:23][CH2:24][N:25]2[C:29](=[O:30])[C:28]3=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]3[C:26]2=[O:35])[N:4]=1

Participants

5

Reactant 3

HCID 93575N-(4-Bromobutyl)phthalimideHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 178507915HCID 178507915, compound

Product 1

HCID 212987544-Amino-2-(4-phthalimidobutylthio)pyrimidineYield 86.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-thiocytosine (0.25 g.), 1,5-diazabicyclo[5,4,0]undec-5-ene (0.33 g.), ethanol (10 ml.) and N-(4-bromobutyl)phthalimide (0.62 g.) was stirred at room temperature for 18 hours and then evaporated to dryness. The residue was partitioned between water and ethyl acetate and the ethyl acetate phase was dried and evaporated to dryness. The residue was recrystallised from acetonitrile to give 4-amino-2-(4-phthalimidobutylthio)pyrimidine (0.56 g.), m.p. 164°-167°.

Workup

  1. customevaporated to dryness
  2. customThe residue was partitioned between water and ethyl acetate
  3. dry with materialthe ethyl acetate phase was dried
  4. customevaporated to dryness
  5. customThe residue was recrystallised from acetonitrile

Sources & evidence

ORD record
ord-a682a20e344347838a09dbb729f50832
Source dataset
uspto-grants-1988_08
Patent number
US04762932

Linked notes

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