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

HRID 364277Notes

Reaction equation

HRID 364277 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-873d04f7bac14798914803a89324da13
Source dataset
uspto-grants-1986_08
Patent number
US04604465

Reaction notes

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