4-Fluorothiophenol → HCID 57427823, compound

HRID 2353728Notes

Reaction equation

HRID 2353728 reaction equation
C1CCN2C(=NCCC2)CC1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1.Cl[CH2:21][C:22]1[NH:27][C:26](=[O:28])[NH:25][C:24](=[O:29])[CH:23]=1>CN(C=O)C>[F:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][CH2:21][C:22]2[NH:27][C:26](=[O:28])[NH:25][C:24](=[O:29])[CH:23]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 677894-FluorothiophenolHCID 732736-(Chloromethyl)-2,4(1H,3H)-pyrimidinedioneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 57427823HCID 57427823, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

DBU (4.02 mL, 26.91 mmol) was added to 4-fluorobenzenethiol (3.45 g, 26.91 mmol), in DMF (90 mL) at RT. The resulting solution was stirred at 20° C. for 15 minutes. 6-(Chloromethyl)-1H-pyrimidine-2,4-dione (2.88 g, 17.94 mmol) was then added and the reaction stirred for 4 hours. The reaction mixture was concentrated and diluted with DCM (100 mL), and washed with water (100 mL). The aqueous layer was acidified with 2M hydrochloric acid to give a white solid which was filtered and washed with water then dried under vacuum to give desired product (2.5 g).

Workup

  1. stirringthe reaction stirred for 4 hours
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with DCM (100 mL)
  4. washwashed with water (100 mL)
  5. customto give a white solid which
  6. filtrationwas filtered
  7. washwashed with water
  8. customthen dried under vacuum

Sources & evidence

ORD record
ord-374b402fced84fc6b4982edb75d7530e
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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