6-Methylamino-4-(quinolin-6-yloxy)-pyrimidine → 6-Methylamino-4-(1,2,3,4-tetrahydro-quinolin-6-yloxy)-pyrimidine

HRID 2264571Notes

Reaction equation

HRID 2264571 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:4]=1>C1COCC1.C(O)(=O)C.O=[Pt]=O>[CH3:1][NH:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH2:15][CH2:14][CH2:13]3)[CH:4]=1

Participants

4

Reactant 1

HCID 675302226-Methylamino-4-(quinolin-6-yloxy)-pyrimidine

Product 1

HCID 675311756-Methylamino-4-(1,2,3,4-tetrahydro-quinolin-6-yloxy)-pyrimidine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 23444217Acetic acid tetrahydrofuranSolvent

Procedure

In the presence of 1 g of PtO2 (Engelhard 7018), a solution of 2.63 g (10.4 mM) 6-methylamino-4-(quinolin-6-yloxy)-pyrimidine in 175 ml of THF/acetic acid 4:1 is hydrogenated. The catalyst is filtered off and the filtrate concentrated in vacuo. The residue is diluted with EtOAc and sat. Na2CO3 solution and extracted 3× with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and partially concentrated in vacuo. The crystallized title compound can be filtered off and washed with EtOAc and DIPE: TLC(EtOAc): Rf=0.18; MS: [M+1]+=257. More product can be isolated from the filtrate by column chromatography (SiO2; EtOAc).

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate concentrated in vacuo
  3. additionThe residue is diluted with EtOAc and sat. Na2CO3 solution
  4. extractionextracted 3× with EtOAc
  5. washThe organic phases are washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationpartially concentrated in vacuo
  8. customThe crystallized title compound
  9. filtrationcan be filtered off
  10. washwashed with EtOAc and DIPE
  11. customMore product can be isolated from the filtrate by column chromatography (SiO2; EtOAc)

Sources & evidence

ORD record
ord-9a2a9f3bf2604f39a47e33a8e1f9638b
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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