Hydrogen Bromide → 6-(2-bromoethyl)-2,3-dihydro-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one monohydrobromide

HRID 1980119Notes

Reaction equation

HRID 1980119 reaction equation
O[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][S:13][C:7]2=[N:6][C:5]=1[CH3:14].[BrH:15]>C(O)(=O)C>[BrH:15].[Br:15][CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][S:13][C:7]2=[N:6][C:5]=1[CH3:14]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 155864626-(2-Hydroxyethyl)-7-methyl-2H-thiazolo[3,2-a]pyrimidin-5(3H)-one

Product 1

HCID 155864646-(2-bromoethyl)-2,3-dihydro-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one monohydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To 79.6 parts of 2,3-dihydro-6-(2-hydroxyethyl)-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one were added dropwise successively 95 parts of acetic acid and 303 parts of a hydrobromic acid solution 30% in acetic acid at a temperature below 45° C. Upon completion, the whole was heated to reflux and stirring was continued for 17.25 hours at reflux temperature. The reaction mixture was cooled to room temperature. The precipitated product was filtered off and stirred in 152 parts of 2-propanol. The product was filtered off, washed with 40 parts of 2-propanol, dried in vacuo at 50° C. and recrystallized from methanol, yielding 102.3 parts of 6-(2-bromoethyl)-2,3-dihydro-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one monohydrobromide; mp. 237.2° C. (intermediate 4).

Workup

  1. temperatureUpon completion, the whole was heated
  2. temperatureto reflux
  3. temperatureat reflux temperature
  4. filtrationThe precipitated product was filtered off
  5. stirringstirred in 152 parts of 2-propanol
  6. filtrationThe product was filtered off
  7. washwashed with 40 parts of 2-propanol
  8. customdried in vacuo at 50° C.
  9. customrecrystallized from methanol

Sources & evidence

ORD record
ord-45007d02314644fb9813b5566cb72a6b
Source dataset
uspto-grants-1984_11
Patent number
US04485107

Reaction notes

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