Perchloric Acid → HCID 178507947, compound

HRID 2386685Notes

Reaction equation

HRID 2386685 reaction equation
Cl(O)(=O)(=O)=O.COC1C=CC(C[N:13](CC2C=CC(OC)=CC=2)[C:14]2[C:23]3[CH:22]=[N:21][C:20]([NH:24][CH:25]4[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]4)=[N:19][C:18]=3[N:17]([CH:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[C:16](=[O:37])[CH:15]=2)=CC=1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[NH2:13][C:14]1[C:23]2[CH:22]=[N:21][C:20]([NH:24][C@H:25]3[CH2:26][CH2:27][C@H:28]([OH:31])[CH2:29][CH2:30]3)=[N:19][C:18]=2[N:17]([CH:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)[C:16](=[O:37])[CH:15]=1

Participants

5

Reactant 2

HCID 24247Perchloric AcidHCID 57929458HCID 57929458, compound

Product 1

HCID 178507947HCID 178507947, compoundYield 106.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Perchloric acid (0.1 mL) was slowly added at RT to a solution of 5-[bis-(4-methoxy-benzyl)-amino]-8-cyclopentyl-2-(4-hydroxy-cyclohexylamino)-8H-pyrido[2,3-d]pyrimidin-7-one (51 mg, 0.087 mmol) in DCM (0.9 mL) and the resulting mixture was stirred at RT for 20 min. The reaction mixture was then diluted with DCM and NaHCO3 (sat'd aq) was slowly added. The organic layer was washed 4 times with NaHCO3 (sat'd aq). The combined aqueous layers were extracted 3 times with DCM and once with a mixture of chloroform and isopropanol. The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified by preparative TLC (DCM/MeOH 90/10) to afford 31.9 mg of trans-5-amino-8-cyclopentyl-2-(4-hydroxy-cyclohexylamino)-8H-pyrido[2,3-d]pyrimidin-7-one as a yellow solid. MS=344 [M+H]+; MP=246.5-248.0° C.

Workup

  1. additionwas slowly added
  2. washThe organic layer was washed 4 times with NaHCO3 (sat'd aq)
  3. extractionThe combined aqueous layers were extracted 3 times with DCM
  4. additiononce with a mixture of chloroform and isopropanol
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude residue was purified by preparative TLC (DCM/MeOH 90/10)

Sources & evidence

ORD record
ord-8c138f46b77b42b6b6cf307241ee82c6
Source dataset
uspto-grants-2012_09
Patent number
US08268840B2

Reaction notes

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