Bromine → 7-bromo-6-chlorothieno[3,2-d]pyrimidin-4(3H)-one

HRID 2291664Notes

Reaction equation

HRID 2291664 reaction equation
[Cl:1][C:2]1[S:10][C:9]2[C:8](=[O:11])[NH:7][CH:6]=[N:5][C:4]=2[CH:3]=1.[Br:12]Br>C(O)(=O)C>[Br:12][C:3]1[C:4]2[N:5]=[CH:6][NH:7][C:8](=[O:11])[C:9]=2[S:10][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 1355834876-chlorothieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 1355834887-bromo-6-chlorothieno[3,2-d]pyrimidin-4(3H)-oneYield 44%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1.12 g (0.006 mole) of 6-chlorothieno[3,2-d]pyrimidin-4(3H)-one and 15 ml of acetic acid at 80° C. was treated with 2.88 g (0.92 ml, 0.018 mole) of bromine. Heating was continued for 2.5 hours during which time solids precipitated. After cooling to room temperature, the mixture was filtered and washed with acetic acid, water and acetone. There was obtained 0.70 g (44%) of the title compound: m.p. above 280° C.; mass spectrum 264 (molecular ion and parent peak with expected isotope pattern), 239 (-27), 186 (some starting material) among others; 1H-nmr (trifluoroacetic acid) delta 7.5 ppm (starting material, s 0.1 H), 9.3 (s, 1.0H). The nmr spectrum indicates that the reaction product is about 90% of the desired product; the remainder is starting material. This material is sufficiently pure for use in further reactions.

Workup

  1. temperatureHeating
  2. customprecipitated
  3. filtrationthe mixture was filtered
  4. washwashed with acetic acid, water and acetone

Sources & evidence

ORD record
ord-9750ba485e6447d5905d4dbc4cd598d5
Source dataset
uspto-grants-1989_01
Patent number
US04797486

Reaction notes

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