Trifluoroacetic acid → HCID 86731165, compound

HRID 920673Notes

Reaction equation

HRID 920673 reaction equation
[CH2:1]([NH:5][C:6]1[N:7]=[CH:8][C:9]2[N:14](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:13]=[C:12]([C:34]3[CH2:39][CH2:38][CH:37]([O:40][Si](C(C)(C)C)(C)C)[CH2:36][CH:35]=3)[C:10]=2[N:11]=1)[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH2:1]([NH:5][C:6]1[N:7]=[CH:8][C:9]2[NH:14][CH:13]=[C:12]([CH:34]3[CH2:35][CH2:36][CH:37]([OH:40])[CH2:38][CH2:39]3)[C:10]=2[N:11]=1)[CH2:2][CH2:3][CH3:4].[CH2:1]([NH:5][C:6]1[N:7]=[CH:8][C:9]2[NH:14][CH:13]=[C:12]([CH:34]3[CH2:39][CH2:38][C:37](=[O:40])[CH2:36][CH2:35]3)[C:10]=2[N:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 86731167HCID 86731167, compoundHCID 178418287HCID 178418287, compound

Product 2

HCID 86731165HCID 86731165, compoundHCID 86731166HCID 86731166, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-Butyl-7-(4-((tert-butyldimethylsilyl)oxy)cyclohex-1-en-1-yl)-5-trityl-5H-pyrrolo[3,2-d]pyrim-idin-2-amine (992 mg, 1.54 mmol) in CH2Cl2 (20 mL) was added trifluoroacetic acid (5.0 mL). The reaction mixture was stirred for 4 hours and quenched by a saturated aq. solution of NaHCO3 and diluted with EtOAc. The organic layer was dried (MgSO4), filtered and concentrated. The residue was dissolved in MeOH (6.0 mL) and Pd/C (44 mg) was added. The reaction mixture was then stirred under the hydrogen atmosphere for 12 hours and then filtered. The filtrate was concentrated to afford a brown residue. A solution of the residue in CH2Cl2 (10 mL) was added a mixture of PCC (665 Mg, 3.084 mmol) and silica gel (668 mg). After 30 min, the reaction was quenched with water and extracted with EtOAc (3×). The combined organic layer was dried (MgSO4), filtered and concentrated. The residue was purified by ISCO to provide the desired product 4-(2-(butylamino)-5H-pyrrolo[3,2-d]pyrimidin-7-yl)cyclohexanone (MS m/z 287.2 [M+H]+). A solution of 4-(2-(butylamino)-5H-pyrrolo[3,2-d]pyrimidin-7-yl)cyclohexanone in MeOH (10 mL) was added NaBH4 (67 mg, 1.71 mmol) slowly at −40° C. The reaction was quenched with water after 1 h and extracted with EtOAc (3×). The combined organic layer was dried (MgSO4), filtered and concentrated. The residue was purified by ISCO to provide the desired product which was used without further purification. MS m/z 289.2 [M+H]+.

Workup

  1. customquenched by a saturated aq. solution of NaHCO3
  2. additiondiluted with EtOAc
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in MeOH (6.0 mL)
  7. additionPd/C (44 mg) was added
  8. stirringThe reaction mixture was then stirred under the hydrogen atmosphere for 12 hours
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated
  11. customto afford a brown residue
  12. waitAfter 30 min
  13. customthe reaction was quenched with water
  14. extractionextracted with EtOAc (3×)
  15. dry with materialThe combined organic layer was dried (MgSO4)
  16. filtrationfiltered
  17. concentrationconcentrated
  18. customThe residue was purified by ISCO

Sources & evidence

ORD record
ord-e9a29c688c5e4d96b42f743272a6bd23
Source dataset
uspto-grants-2016_03
Patent number
US09273056B2

Reaction notes

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