Diisopropylethylamine → HCID 118598802, compound

HRID 1050351Notes

Reaction equation

HRID 1050351 reaction equation
[CH:1]1([C:4]2[N:13]=[CH:12][C:11]3[C:10](=O)[NH:9][CH:8]=[N:7][C:6]=3[CH:5]=2)[CH2:3][CH2:2]1.C([N:18](CC)C(C)C)(C)C.O(Cl)Cl.[P+5]>>[CH:1]1([C:4]2[N:13]=[CH:12][C:11]3[C:10]([NH2:18])=[N:9][CH:8]=[N:7][C:6]=3[CH:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 136980668HCID 136980668, compoundHCID 178479711HCID 178479711, compound

Product 1

HCID 118598802HCID 118598802, compound

Procedure

To 7-cyclopropyl-3H-pyrido[4,3-d]pyrimidin-4-one (7, 1.0 g, 5.34 mmol) in a round bottom flask under a nitrogen atmosphere was added N,N-diisopropylethylamine (9.45 mL, 53.42 mmol) at 0° C. To this stirred mixture was slowly added phosphorus(V) oxychloride (7.48 mL, 80.13 mmol). The reaction mixture was stirred at room temperature for 2-3 h until a clear solution was obtained. The solution was concentrated under reduced pressure under inert conditions, taken up in excess toluene and reconcentrated. This process was repeated sev N,N-diisopropylethylamine eral times. The residue was dissolved in acetonitrile to it was added 30% aqueous ammonia (30 mL). The mixture was heated to 120° C. for 16 h in sealed tube. The reaction mixture was diluted with 10% methanol in dichloromethane and extracted from the aqueous ammonia. The organic layers were separated, dried over Sodium sulfate, filtered and concentrated to dryness. The crude residue was given Methanol washing. The solid obtained was dried to afford 7-cyclopropylpyrido[4,3-d]pyrimidin-4-amine (8) as a brown solid. Yield: 0.60 g, 60%; MS (ESI) m/z 375.8 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 9.34 (s, 1H), 8.43 (s, 1H), 8.26-7.99 (m, 2H), 7.39 (s, 1H), 1.75 (s, 1H), 1.01-0.84 (s, 4H).

Workup

  1. customwas obtained
  2. concentrationThe solution was concentrated under reduced pressure under inert conditions
  3. dissolutionThe residue was dissolved in acetonitrile to it
  4. additionwas added 30% aqueous ammonia (30 mL)
  5. temperatureThe mixture was heated to 120° C. for 16 h in sealed tube
  6. additionThe reaction mixture was diluted with 10% methanol in dichloromethane
  7. extractionextracted from the aqueous ammonia
  8. customThe organic layers were separated
  9. dry with materialdried over Sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated to dryness
  12. customThe solid obtained
  13. customwas dried

Sources & evidence

ORD record
ord-8baec8f6a07f4878b582fe540168062f
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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