Water → 7-amino-4-([R]-1-phenylethylamino)pyrido[4,3-d]pyrimidine

HRID 2287714Notes

Reaction equation

HRID 2287714 reaction equation
[C:1]1([C@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][C:11]1[N:20]=[CH:19][C:18]2[C:17](SC)=[N:16][CH:15]=[N:14][C:13]=2[CH:12]=1.O>C(Cl)(Cl)Cl>[NH2:10][C:11]1[N:20]=[CH:19][C:18]2[C:17]([NH:9][C@@H:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH3:8])=[N:16][CH:15]=[N:14][C:13]=2[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6431891-Phenethylamine, (+)-HCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 539624137-amino-4-([R]-1-phenylethylamino)pyrido[4,3-d]pyrimidineYield 11%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of [R]-1-phenylethylamine (0.072 mL, 0.55 mmol) and 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (97 mg, 0.5 mmol) (described in a previous experimental) is heated at 180° C. under N2 for 1.5 hr. The reaction is then cooled to room temperature producing a precipitate. The mixture is added to water and CHCl3, sonicated and filtered. The phases are separated and the aqueous phase is extracted with CHCl3. The combined extracts are washed with water, saturated brine and dried (MgSO4). The solvent is removed under reduced pressure and the residue purified by using preparative tlc (5% MeOH/CHCl3) and recrystallization from CHCl3 to give 7-amino-4-([R]-1-phenylethylamino)pyrido[4,3-d]pyrimidine (14.5 mg, 11%), mp 231.8-232.1° C. 1H NMR (DMSO) δ 9.23 (1H, s), 8.50 (1H, d, J=8.0 Hz), 8.19 (1H, s), 7.41 (2H, d, J=7.0 Hz), 7.31 (2H, t, J=8.0 Hz, 7.21 (1H, tt, J=7.4, 1.2 Hz), 6.45 (2H, s), 6.33 (1H, s), 5.56 (1H, p, J=7.2 Hz), 1.55 (3H, d, J=7.0 Hz).

Workup

  1. temperatureThe reaction is then cooled to room temperature
  2. customproducing a precipitate
  3. customsonicated
  4. filtrationfiltered
  5. customThe phases are separated
  6. extractionthe aqueous phase is extracted with CHCl3
  7. washThe combined extracts are washed with water, saturated brine
  8. dry with materialdried (MgSO4)
  9. customThe solvent is removed under reduced pressure
  10. customthe residue purified
  11. customtlc (5% MeOH/CHCl3) and recrystallization from CHCl3

Sources & evidence

ORD record
ord-5f5be9cf4d0f45d0a02523757cd9ff9c
Source dataset
uspto-grants-2000_07
Patent number
US06084095

Reaction notes

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