Trifluoroacetic acid → 5H,6H,7H,8H-pyrido(4,3-d)pyrimidine

HRID 132860Notes

Reaction equation

HRID 132860 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:11]2[N:12]=[CH:13][N:14]=[CH:15][C:10]=2[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[N:12]1[C:11]2[CH2:16][CH2:17][NH:8][CH2:9][C:10]=2[CH:15]=[N:14][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22707088tert-Butyl 7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Product 1

HCID 109326745H,6H,7H,8H-pyrido(4,3-d)pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from Step B above (730 mg) in 10 mL of dichloromethane was cooled to 0° C. and treated dropwise with 5 mL of trifluoroacetic acid. The solution was warmed to room temperature and, after 1 h, concentrated under reduced pressure. The residue was dissolved in methanol and applied to an ion-exchange column (Varian Bond-Elut SCX, 5 g; preconditioned with methanol). The column was washed several times with methanol, and the amine product was eluted with 1.0M ammonia-methanol. The fractions containing product were concentrated under reduced pressure to afford the title compound as an orange oil. LC/MS 136.1 (M+1).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol
  3. washThe column was washed several times with methanol
  4. washthe amine product was eluted with 1.0M ammonia-methanol
  5. additionThe fractions containing product
  6. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-8ded603b58534a65bf603ac9bf519099
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Reaction notes

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