Triethylamine → HCID 12791254, compound

HRID 1906160Notes

Reaction equation

HRID 1906160 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.Br[CH2:10][C:11]([C:13]1[S:17][C:16]2[CH2:18][CH2:19][CH2:20][CH2:21][C:15]=2[CH:14]=1)=[O:12].C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH2:10][C:11]([C:13]2[S:17][C:16]3[CH2:18][CH2:19][CH2:20][CH2:21][C:15]=3[CH:14]=2)=[O:12])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 20212806HCID 20212806, compound

Product 1

HCID 12791254HCID 12791254, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-chloropyrimidin-2-one (370 mg) and 2-bromoacetyl-4,5,6,7-tetrahydrobenzo[b]thiophene (740 mg) in ethanol (15 ml) was treated with triethylamine (0.6 ml, 4.76 mmol) and then stirred at room temperature. After 1.5 h the mixture was concentrated to ca 5 ml and then diluted with ethyl acetate (50 ml). The resulting solution was washed with water (×3), dried (MgSO4) and evaporated to a pale yellow foam. The foam was subjected to preparative thin-layer chromatography on silica developing with chloroform-ethanol (29:1) (two runs). Elution of the major band with ethyl acetate gave a white solid which was crystallised from ethyl acetate to give the title pyrimidinone (290 mg), m.p. 206°-208° C., λmax (EtOH) 225 nm (ε 10,160), 268.5 nm (ε 9,570), 314 nm (ε 12,260).

Workup

  1. concentrationAfter 1.5 h the mixture was concentrated to ca 5 ml
  2. additiondiluted with ethyl acetate (50 ml)
  3. washThe resulting solution was washed with water (×3)
  4. dry with materialdried (MgSO4)
  5. customevaporated to a pale yellow foam
  6. washElution of the major band with ethyl acetate
  7. customgave a white solid which
  8. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-c9c472afa8404ac99194673bb65d584e
Source dataset
uspto-grants-1987_03
Patent number
US04650800

Reaction notes

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