Hydrochloric Acid → HCID 46865656, compound

HRID 1260398Notes

Reaction equation

HRID 1260398 reaction equation
[NH2:1][C:2]([C:4]1[C:5]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)=[N:6][C:7]([NH:10][C@@H:11]2[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]2[NH:17]C(=O)OC(C)(C)C)=[N:8][CH:9]=1)=[O:3].Cl.[OH-].[Na+]>C(O)(C)C.C(O)C>[NH2:17][C@@H:12]1[C@H:11]([NH:10][C:7]2[N:6]=[C:5]([NH:25][C:26]3[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=3)[C:4]([C:2]([NH2:1])=[O:3])=[CH:9][N:8]=2)[CH2:16][CH2:15][O:14][CH2:13]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 706681481,1-Dimethylethyl N-[(3R,4R)-4-[[5-(aminocarbonyl)-4-[(4-methylphenyl)amino]-2-pyrimidinyl]amino]tetrahydro-2H-pyran-3-yl]carbamate

Product 1

HCID 46865656HCID 46865656, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

1,1-Dimethylethyl [(3R,4R)-4-({5-(aminocarbonyl)-4-[(4-methylphenyl)amino]-2-pyrimidinyl}amino)tetrahydro-2H-pyran-3-yl]carbamate (52.2 g) was added to a mixture of hydrogen chloride in isopropanol (5M, 300 ml) and ethanol (400 ml). The mixture was heated to reflux while stirring and heating continued for 24 h with vigorous stirring. The mixture was allowed to cool to room temperature, filtered, the solid washed with ethanol (100 ml) and dried in vacuo. The crude product was suspended in water (900 ml) and heated to reflux, giving a clear solution. The solution was basified with sodium hydroxide solution (2M, 300 ml) and cooled in ice. The precipitated product was collected by filtration, washed with water (2×100 ml) and the beige solid dried in the vacuum oven at 40° C. for 2 h to give 2-{[(3R,4R)-3-aminotetrahydro-2H-pyran-4-yl]amino}-4-[(4-methylphenyl)amino]-5-pyrimidinecarboxamide as beige solid (37.8 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureheating
  4. filtrationfiltered
  5. washthe solid washed with ethanol (100 ml)
  6. customdried in vacuo
  7. temperatureheated
  8. temperatureto reflux
  9. customgiving a clear solution
  10. temperaturecooled in ice
  11. filtrationThe precipitated product was collected by filtration
  12. washwashed with water (2×100 ml)
  13. customthe beige solid dried in the vacuum oven at 40° C. for 2 h

Sources & evidence

ORD record
ord-dd25f5effbe5494fbe7ef660f773ba36
Source dataset
uspto-grants-2013_06
Patent number
US08470835B2

Reaction notes

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