Hydrochloric Acid → N-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

HRID 930497Notes

Reaction equation

HRID 930497 reaction equation
[NH:1]([C:8]1[N:9]=[CH:10][C:11]2[CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14][C:12]=2[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CC(C)=O.CC(O)C>[C:2]1([NH:1][C:8]2[N:9]=[CH:10][C:11]3[CH2:17][NH:16][CH2:15][CH2:14][C:12]=3[N:13]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 45106267t-butyl 2-anilino-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Product 1

HCID 104609480N-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Procedure

A solution of t-butyl 2-anilino-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate, Intermediate 7 (2.51 g, 7.69 mmol) in acetone (20 mL) was treated with 5-6 N HCl solution in i-PrOH (6 mL) and the reaction mixture was stirred at room temperature for 27 hours. The solvent was removed in vacuo and the salt was dissolved in water. The aqueous layer was washed with EtOAc and basified with 1.0 N NaOH(aq). The alkaline mixture was extracted with CH2Cl2 (2×100 mL) and the combined CH2Cl2 extracts were dried (MgSO4), filtered, and concentrated to a yellow, crystalline solid (1.25 g, 72%).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe salt was dissolved in water
  3. washThe aqueous layer was washed with EtOAc
  4. extractionThe alkaline mixture was extracted with CH2Cl2 (2×100 mL)
  5. dry with materialthe combined CH2Cl2 extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to a yellow, crystalline solid (1.25 g, 72%)

Sources & evidence

ORD record
ord-5575d9c12b7741a5b3d6eff9fb0ce7ee
Source dataset
uspto-grants-2016_03
Patent number
US09296747B1

Reaction notes

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