Dichloromethane → (2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)(piperidin-4-yl)methanol

HRID 1923223Notes

Reaction equation

HRID 1923223 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([CH:18]([OH:32])[CH:19]4[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]4)[N:14]3[CH3:17])=[C:10]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[N:9]=2)[C:6]2[CH:39]=[CH:40][CH:41]=[CH:42][C:5]=2[N:4]=1)[CH3:2].C(Cl)Cl.FC(F)(F)C(O)=O>>[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([CH:18]([CH:19]4[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]4)[OH:32])[N:14]3[CH3:17])=[C:10]([N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)[N:9]=2)[C:6]2[CH:39]=[CH:40][CH:41]=[CH:42][C:5]=2[N:4]=1)[CH3:2]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 67492684tert-butyl 4-((2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)(hydroxy)methyl)piperidine-1-carboxylate

Product 1

HCID 59605474(2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)(piperidin-4-yl)methanol

Procedure

To a solution of tert-butyl 4-((2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)(hydroxy)methyl)piperidine-1-carboxylate (0.320 g, 0.555 mmol) in Methylene chloride (10 mL, 200 mmol;) was added Trifluoroacetic Acid (0.50 mL, 6.5 mmol;). The reaction was stirred at room temperature for 1 hr. and the reaction mixture was evaporated to dryness. To the residue was added 2M NH3 in MeOH to neutralize any residual acid. The mixture was then evaporated to dryness. The crude was then purified by flash chromatography (0-15% MeOH in DCM) to give the desired product as pinkish paste (0.24 g, 91%). LCMS m/z 477.4 (MH+).

Workup

  1. customand the reaction mixture was evaporated to dryness
  2. additionTo the residue was added 2M NH3 in MeOH
  3. customThe mixture was then evaporated to dryness
  4. customThe crude was then purified by flash chromatography (0-15% MeOH in DCM)

Sources & evidence

ORD record
ord-c547d086214e4d55962c807368b9eb0c
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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