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

HRID 1386180Notes

Reaction equation

HRID 1386180 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 10.9%

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 tic (5% MeOH/CHCl3) and recrystallization from CHCl3 to give 7-amino-4-([R]-1-phenylethylamino)pyrido[4,3-d]pyrimidine (14.5 mg, 1l;), 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. customtic (5% MeOH/CHCl3) and recrystallization from CHCl3

Sources & evidence

ORD record
ord-ac8b6f19597e42a5bd9a2e33ac694e6d
Source dataset
uspto-grants-2001_07
Patent number
US06265410B1

Reaction notes

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