5-Chloro-2(1H)-pyrimidinethione → HCID 20475714, compound

HRID 905226Notes

Reaction equation

HRID 905226 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[S:8])[NH:6][CH:7]=1.CC(C)([O-])C.[K+].Cl[CH2:16][CH2:17][CH2:18][N:19]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C=O)C>[N:19]1([CH2:18][CH2:17][CH2:16][S:8][C:5]2[N:6]=[CH:7][C:2]([Cl:1])=[CH:3][N:4]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 71403455-Chloro-2(1H)-pyrimidinethioneHCID 12323624HCID 12323624, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20475714HCID 20475714, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

5-Chloropyrimidine-2-thione (2 mmol) and potassium tert-butoxide (2 mmol) was stirred together in DMF (20 ml) for 5 min at room temperature before 1-(3-chloropropyl)perhydroazocine (2 mmol) was added. The mixture was stirred for 2 days at room temperature and for 2 hours at 80° C. The solution was evaporated, the residue triturated with water, extracted with chloroform and the dried (MgSO4) chloroform solution evaporated. The oily product which remained (0.47 g) was the title compound; yield 45% 1H NMR (CDCl3): 1.3-2.8 (9×CH2), 3.20 (SCH2), 8.40 (H-4, H-6). The compound was further characterized as a solid by conversion into its HCl salt using HCl in ethanol; m.p. 154° C. (acetone).

Workup

  1. additionwas added
  2. customThe solution was evaporated
  3. customthe residue triturated with water
  4. extractionextracted with chloroform
  5. dry with materialthe dried (MgSO4) chloroform solution
  6. customevaporated

Sources & evidence

ORD record
ord-a0012aaffe094c97894108d85236e3c8
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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