Acetic Acid → 2-Bromo-1-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)ethanone

HRID 2098878Notes

Reaction equation

HRID 2098878 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([C:11](=[O:13])[CH3:12])=[CH:8][C:6]=2[N:7]=1.[BrH:20].C(O)(=O)C.BrBr>C(Cl)(Cl)Cl>[Br:20][CH2:12][C:11]([C:9]1[S:10][C:5]2[C:4]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[N:3][C:2]([Cl:1])=[N:7][C:6]=2[CH:8]=1)=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 24408BromineHCID 595931571-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)ethanone

Product 1

HCID 595929052-Bromo-1-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)ethanone (1.0 eq) dissolved in a mixture of CHCl3, 33% wt HBr and acetic acid (1:1:1) at −0° C. was added a solution of Br2 in CHCl3 (1.05 eq). Reaction mixture was stirred at −0° C. until completed, then extracted in dichloromethane with saturated bicarbonate solution one time. The organic layer is dried, filtered and concentrated to yield the crude intermediate. This intermediate is purified by flash chromatography to yield 2-bromo-1-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)ethanone.

Workup

  1. customat −0° C.
  2. customReaction mixture
  3. extractionextracted in dichloromethane with saturated bicarbonate solution one time
  4. customThe organic layer is dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield the crude intermediate
  8. customThis intermediate is purified by flash chromatography

Sources & evidence

ORD record
ord-cc4a6bdf82c149d69f12fdcdd3291523
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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