Trifluoroacetic acid methylene chloride → 2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-amine

HRID 2262080Notes

Reaction equation

HRID 2262080 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:5]2[S:10][C:9]([NH:11]C(=O)OC(C)(C)C)=[CH:8][C:6]=2[N:7]=1.FC(F)(F)C(O)=O.ClCCl>>[Cl:1][C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:5]2[S:10][C:9]([NH2:11])=[CH:8][C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 59592872Tert-butyl 2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-ylcarbamate

Product 1

HCID 595928682-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-amineYield 99.3%

Procedure

Tert-butyl 2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-ylcarbamate (800 mg) was treated with 5 mL of trifluoroacetic acid/dichloromethane (1:1). The reaction mixture was stirred at room temperature until complete. The reaction mixture was evaporated. The residue was diluted with ethyl acetate (100 mL), washed with saturated sodium bicarbonate (50 mL) and brine (50 mL). The aqueous layer was back-extracted with ethyl acetate (2×60 mL), and then washed with saturated sodium bicarbonate and brine. The combined organic layers were dried over MgSO4, filtered and evaporated to afford 580 mg of 2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-amine.

Workup

  1. customThe reaction mixture was evaporated
  2. additionThe residue was diluted with ethyl acetate (100 mL)
  3. washwashed with saturated sodium bicarbonate (50 mL) and brine (50 mL)
  4. extractionThe aqueous layer was back-extracted with ethyl acetate (2×60 mL)
  5. washwashed with saturated sodium bicarbonate and brine
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-cb63971dd022422996768e312a513cab
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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