Acetic Acid → HCID 9957270, compound

HRID 1375422Notes

Reaction equation

HRID 1375422 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[CH2:19][CH2:18][CH:17]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[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]([NH:20][CH:17]1[CH2:18][CH2:19][N:15]([C:12]2[CH:11]=[CH:10][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:14][CH:13]=2)[CH2:16]1)=[O:22])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 80521Butyl oxoacetateHCID 58786810HCID 58786810, compound

Product 1

HCID 9957270HCID 9957270, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.70 g (1.5 mmol) of 5-amino-2-[[4-[3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]phenyl]amino]-4-(cyclopentylamino)-pyrimidine, 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), gives 0.21 g (28%) of the title compound (Compound 53): mp (MeOH) 226–228° 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-9e5a8f6ea7554518a36d86839fbf140a
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Reaction notes

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