Acetic Acid → 2-[[4-[4(Tert-butoxycarbonyl)piperazin-1-yl]phenyl]amino]-8-cyclopentyl-8h-pteridin-7-one

HRID 1375421Notes

Reaction equation

HRID 1375421 reaction equation
[NH2:1][C:2]1[C:3]([NH:28][CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[C:34](OCCCC)(=O)[CH:35]=[O:36].CC(O)=O>CCO>[C:24]([O:23][C:21]([N:18]1[CH2:19][CH2:20][N:15]([C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:5]3[N:6]=[CH:7][C:2]4[N:1]=[CH:34][C:35](=[O:36])[N:28]([CH:29]5[CH2:30][CH2:31][CH2:32][CH2:33]5)[C:3]=4[N:4]=3)=[CH:10][CH:11]=2)[CH2:16][CH2:17]1)=[O:22])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 80521Butyl oxoacetateHCID 587867835-Amino-2-[[4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl]amino]-4-(cyclopentylamino)pyrimidine

Product 1

HCID 99353632-[[4-[4(Tert-butoxycarbonyl)piperazin-1-yl]phenyl]amino]-8-cyclopentyl-8h-pteridin-7-oneYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.82 g (1.8 mmol) of 5-amino-2-[[4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl]amino]-4-(cyclopentylamino)pyrimidine (from preparation 14A), 0.52 g (4 mmol) of butyl glyoxylate (F. J. Wolf, J. Weijlard, Org. Synth. Coll., 1963;4:124–125), and 0.5 mL HOAc in 15 mL of EtOH is heated under reflux for 14 hours, and the solvent is removed under vacuum. The residue is diluted with aqueous ammonia solution and extracted into EtOAc. Chromatography on silica, eluting with hexane/EtOAc (3:2) gave 0.38 g (43%) of the title compound (Compound 52): mp (MeOH) 215–217° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 14 hours
  3. customthe solvent is removed under vacuum
  4. additionThe residue is diluted with aqueous ammonia solution
  5. extractionextracted into EtOAc
  6. washChromatography on silica, eluting with hexane/EtOAc (3:2)

Sources & evidence

ORD record
ord-4e809fc02d4849989c58b13198046607
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Reaction notes

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