Hydrochloric Acid → HCID 11283931, compound

HRID 2422150Notes

Reaction equation

HRID 2422150 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9]([O:11]C)=[O:10])=[C:6]([N:13]([CH2:15][C:16]([NH:18][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:17])[CH3:14])[N:5]=[C:4]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([NH:31][CH2:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:27][CH:26]=2)[N:3]=1.[OH-].[Na+].Cl>C1COCC1>[Cl:1][C:2]1[C:7]([CH2:8][C:9]([OH:11])=[O:10])=[C:6]([N:13]([CH2:15][C:16]([NH:18][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)=[O:17])[CH3:14])[N:5]=[C:4]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([NH:31][CH2:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:29][CH:30]=2)[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59514536HCID 59514536, compound

Product 1

HCID 11283931HCID 11283931, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl {4-chloro-2-{4-[(cyclohexylmethyl)amino]benzyl}-6-[[2-(cyclopentyl-amino)-2-oxoethyl](methyl)amino]pyrimidin-5-yl}acetate (0.083 g, 0.15 mmol) in THF (5 mL) was treated with 1N NaOH (2.5 mL) and the resulting mixture was stirred at room temperature for 13 hours. Subsequent to neutralization with 6N HCl, the quenched reaction mixture was evaporated to dryness and the remaining residue dissolved with EtOH. The insoluble inorganic salts were removed by filtration and the filtrate was concentrated in vacuo. The crude product thus obtained was purified with preparative TLC eluting with 15% EtOH in CH2Cl2 to give {4-chloro-2-{4-[(cyclohexylmethyl)amino]benzyl}-6-[[2-(cyclopentylamino)-2-oxoethyl](methyl)amino]-pyrimidin-5-yl}acetic acid (0.023 g, 28% yield) as a clear oil.

Workup

  1. customthe quenched reaction mixture
  2. customwas evaporated to dryness
  3. dissolutionthe remaining residue dissolved with EtOH
  4. customThe insoluble inorganic salts were removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe crude product thus obtained
  7. customwas purified with preparative TLC
  8. washeluting with 15% EtOH in CH2Cl2

Sources & evidence

ORD record
ord-525ba1660d714edba4c150960bda5c70
Source dataset
uspto-grants-2011_06
Patent number
US07960393B2

Reaction notes

Loading…