Trifluoroacetic acid → HCID 178492152, compound

HRID 421586Notes

Reaction equation

HRID 421586 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[N:10]([C@H:27]2[CH2:32][CH2:31][C@H:30]([C:33](OCC)=[O:34])[CH2:29][CH2:28]2)[C:11]2[C:16]([N:17]=1)=[CH:15][N:14]=[C:13]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[N:12]=2.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O)(C(F)(F)F)=O>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[N:10]([C@H:27]2[CH2:32][CH2:31][C@H:30]([CH2:33][OH:34])[CH2:29][CH2:28]2)[C:11]2[C:16]([N:17]=1)=[CH:15][N:14]=[C:13]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[N:12]=2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21226445Aluminium lithium hydride2×HCID 178472389HCID 178472389, compound

Product 1

HCID 178492152HCID 178492152, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Ethyl 4-{8-[(2-fluorophenyl)amino]-2-[(4-methoxyphenyl)amino]purin-9-yl}-trans-cyclohexanecarboxylate (0.28 g, 0.55 mmol) was dissolved in 9 mL of THF and cooled to 0° C. (under nitrogen atmosphere). 1.38 mL of 1.0M LiAlH4 in THF was added dropwise. The solution turned a dark orange as the LiAlH4 was added. The reaction mixture was stirred for about 5 h and quenched by the addition of 40 mL of water. The reaction was extracted three times with ethyl acetate. Organics were combined and dried with magnesium sulfate, filtered and the solvent was removed in vacuo. The crude reaction mixture was then purified using reverse-phase preparative HPLC (20-80% acetonitrile/water (0.1% TFA) over 30 min) to obtain 0.126 g of the desired product (50% yield) after neutralization of the TFA salt. ES-MS: 463 (M+1).

Workup

  1. additionwas added
  2. customquenched by the addition of 40 mL of water
  3. extractionThe reaction was extracted three times with ethyl acetate
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe crude reaction mixture
  8. customwas then purified
  9. customreverse-phase preparative HPLC (20-80% acetonitrile/water (0.1% TFA) over 30 min)

Sources & evidence

ORD record
ord-000af7a5f8b247079150ab4794609c60
Source dataset
uspto-grants-2012_01
Patent number
US08101588B2

Reaction notes

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