Trifluoroacetic acid → 2-{4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]piperazin-1-yl}-N,N-dimethyl-2-oxoacetamide

HRID 421376Notes

Reaction equation

HRID 421376 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15]1[N:20]=[CH:19][C:18]([C:21]2[N:29]=[C:28]3[C:24]([N:25]=[C:26]([N:35]4[CH2:40][CH2:39][N:38]([C:41](=[O:47])[C:42]([N:44]([CH3:46])[CH3:45])=[O:43])[CH2:37][CH2:36]4)[N:27]3[CH2:30][C:31]([F:34])([F:33])[F:32])=[C:23]([N:48]3[CH2:53][CH2:52][O:51][CH2:50][CH2:49]3)[N:22]=2)=[CH:17][N:16]=1)(C)(C)C>C1(C)C=CC=CC=1>[NH2:14][C:15]1[N:20]=[CH:19][C:18]([C:21]2[N:29]=[C:28]3[C:24]([N:25]=[C:26]([N:35]4[CH2:36][CH2:37][N:38]([C:41](=[O:47])[C:42]([N:44]([CH3:46])[CH3:45])=[O:43])[CH2:39][CH2:40]4)[N:27]3[CH2:30][C:31]([F:33])([F:34])[F:32])=[C:23]([N:48]3[CH2:49][CH2:50][O:51][CH2:52][CH2:53]3)[N:22]=2)=[CH:17][N:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59333553tert-Butyl {5-[8-{4-[(dimethylamino)(oxo)acetyl]piperazin-1-yl}-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-yl}carbamate

Product 1

HCID 593335592-{4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]piperazin-1-yl}-N,N-dimethyl-2-oxoacetamideYield 95.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trifluoroacetic acid (5 ml) was added to tert-butyl{5-[8-{4-[(dimethylamino)(oxo)acetyl]piperazin-1-yl}-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-yl}carbamate (148 mg, 0.22 mmol) and the resulting mixture was stirred for 30 minutes. Toluene was added and the solvent was evaporated under reduced pressure. Hydrochloric acid-methanol was added to the residue and the solvent was evaporated and dried to give the title compound (118 mg, 88%) as a yellow solid.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionHydrochloric acid-methanol was added to the residue
  3. customthe solvent was evaporated
  4. customdried

Sources & evidence

ORD record
ord-5bf7169368e04ebb900466ab97560dce
Source dataset
uspto-grants-2012_01
Patent number
US08097622B2

Reaction notes

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