Trifluoroacetic acid → (S)-3-(2-Amino-5-(3-aminopropyl)-6-methylpyrimidin-4-ylamino)heptan-1-ol

HRID 1617142Notes

Reaction equation

HRID 1617142 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:10][CH2:11][OH:12])[C:5]([CH2:17][CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)=[C:4]([CH3:28])[N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:10][CH2:11][OH:12])[C:5]([CH2:17][CH2:18][CH2:19][NH2:20])=[C:4]([CH3:28])[N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86633396(S)-tert-Butyl 3-(2-amino-4-(1-hydroxyheptan-3-ylamino)-6-methylpyrimidin-5-yl)propylcarbamate

Product 1

HCID 68416454(S)-3-(2-Amino-5-(3-aminopropyl)-6-methylpyrimidin-4-ylamino)heptan-1-olYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from step (viii) (76 mg) was dissolved in DCM (5 mL) and TFA (5 mL) and the mixture stirred at rt for 1 h. The solvent was evaporated and the crude material dissolved in MeOH (5 mL) and purified by SCX. The product was dissolved in THF (10 mL) then lithium hydroxide (12.2 mg) in water (5 mL) was added. The reaction mixture was heated to reflux for 1 h, the solvents were evaporated and the crude product purified by RPHPLC to afford the subtitle product 40 mg.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude material dissolved in MeOH (5 mL)
  3. custompurified by SCX
  4. dissolutionThe product was dissolved in THF (10 mL)
  5. additionlithium hydroxide (12.2 mg) in water (5 mL) was added
  6. temperatureThe reaction mixture was heated
  7. temperatureto reflux for 1 h
  8. customthe solvents were evaporated
  9. customthe crude product purified by RPHPLC

Sources & evidence

ORD record
ord-d40729e66e884aa1abc15c5c3bb40159
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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