Hydrochloric Acid → HCID 11283931, compound

HRID 1159662Notes

Reaction equation

HRID 1159662 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-476628229a4646fe99a3a9681b772557
Source dataset
uspto-grants-2010_10
Patent number
US07812160B2

Reaction notes

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