Chloroacetonitrile → 6-bromo-2-(chloromethyl)thieno[3,2-d]pyrimidin-4(3H)-one

HRID 1409000Notes

Reaction equation

HRID 1409000 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([Br:7])[S:4][C:3]=1[C:8]([O:10]C)=O.[Cl:12][CH2:13][C:14]#[N:15]>Cl.C1(OC)CCCC1>[Br:7][C:5]1[S:4][C:3]2[C:8](=[O:10])[NH:15][C:14]([CH2:13][Cl:12])=[N:1][C:2]=2[CH:6]=1

Participants

4

Reactant 2

HCID 7856ChloroacetonitrileHCID 20158931Methyl 3-amino-5-bromothiophene-2-carboxylate

Product 1

HCID 1363339056-bromo-2-(chloromethyl)thieno[3,2-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 66926893hydrogen chloride CPMESolvent

Procedure

A mixture of methyl 3-amino-5-bromothiophene-2-carboxylate (15 g) produced in Example 1, step C, chloroacetonitrile (12 mL) and 4M hydrochloric acid/cyclopentylmethylether solution (100 mL) was stirred at room temperature for 2 hr, and stirred at 70° C. for 1 hr. The reaction system was concentrated under reduced pressure, and saturated aqueous sodium hydrogen carbonate was added to the residue. The precipitate was collected by filtration and washed with water. The obtained solid was dried at 80° C. for 8 hr under reduced pressure to give the title compound (18 g) as a pale-brown solid.

Workup

  1. stirringstirred at 70° C. for 1 hr
  2. concentrationThe reaction system was concentrated under reduced pressure, and saturated aqueous sodium hydrogen carbonate
  3. additionwas added to the residue
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customThe obtained solid was dried at 80° C. for 8 hr under reduced pressure

Sources & evidence

ORD record
ord-1dfab874043f47ba93aa2278ebc466e7
Source dataset
uspto-grants-2014_12
Patent number
US08921354B2

Reaction notes

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