Lithium Hydroxide → HCID 59446935, compound

HRID 1746647Notes

Reaction equation

HRID 1746647 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[C:4]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[N:3]=1.C(N(CC)CC)C.C1(CNC2N=CN=C(C(OC)=O)C=2)CCCCC1.C1(CNC2N=CN=C(C(OCC)=O)C=2)CCCCC1.[OH-].[Li+]>[Pd].CCO.C1COCC1.CCO.O.O>[CH:14]1([CH2:13][NH:12][C:4]2[N:3]=[CH:2][N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

10

Reactant 5

HCID 3939Lithium HydroxideHCID 8471TriethylamineHCID 59447008HCID 59447008, compound2×HCID 67528758HCID 67528758, compoundHCID 67529209HCID 67529209, compound

Product 1

HCID 59446935HCID 59446935, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

A mixture of methyl 2-chloro-6-[(cyclohexylmethyl)amino]pyrimidine-4-carboxylate (Intermediate 3, 2.25 g; 7.93 mmol), palladium on charcoal and triethylamine (3.32 mL; 23.8 mmol) in EtOH (400 mL) was stirred under an atmosphere of hydrogen. After 2 hours the reaction mixture was filtered on celite and evaporated to give a mixture of methyl 6-[(cyclohexylmethyl)amino]pyrimidine-4-carboxylate and ethyl 6-[(cyclohexylmethyl)amino]pyrimidine-4-carboxylate. The crude mixture was dissolved in a mixture of THF/EtOH/H2O (3/2/1, 84 mL) and treated with an aqueous solution of lithium hydroxide (1N, 16 mL, 16 mmol). The reaction mixture was stirred at RT for 60 minutes. Water was added (50 mL) and the aqueous layer was washed with chloroform. and the aqueous layer was washed with DCM (30 mL). The aqueous layer was acidified to pH 5 by addition of an HCl solution (1N). A precipitate was formed, which was filtered to afford the title compound.

Workup

  1. filtrationAfter 2 hours the reaction mixture was filtered on celite
  2. customevaporated
  3. customto give
  4. stirringThe reaction mixture was stirred at RT for 60 minutes
  5. washthe aqueous layer was washed with chloroform
  6. washand the aqueous layer was washed with DCM (30 mL)
  7. additionThe aqueous layer was acidified to pH 5 by addition of an HCl solution (1N)
  8. customA precipitate was formed
  9. filtrationwhich was filtered

Sources & evidence

ORD record
ord-5660d15f5cc649309d59036089bb628b
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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