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Trifluoroacetic acid → ethyl 2-chloro-4-morpholino-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

HRID 1626657
Notes
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Reaction equation

HRID 1626657 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[N:10]=[C:11]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:12]2[CH2:17][NH:16][CH2:15][C:13]=2[N:14]=1.C(O)(C(F)(F)F)=O.C(N(CC)CC)C.Cl[C:39]([O:41][CH2:42][CH3:43])=[O:40]>CN(C=O)C>[Cl:8][C:9]1[N:10]=[C:11]([N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[C:12]2[CH2:17][N:16]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:15][C:13]=2[N:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 866631634-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)morpholine trifluoroacetate2×

Product 1

HCID 86663171ethyl 2-chloro-4-morpholino-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)morpholine trifluoroacetate (intermediate 20) as a TFA salt (708 mg, 2.0 mmol) in anhydrous DMF (5 ml) was added triethylamine (5550, 4.0 mmol) and the reaction was stirred at RT for two hours. After this time, ethyl chloroformate (228 μl, 2.4 mmol) was added dropwise and the reaction was stirred at RT overnight. The reaction was partitioned between water and ethyl acetate and the aqueous phase was extracted into ethyl acetate. The organic extracts were combined, washed with brine, dried over magnesium sulphate and concentrated in vacuo to afford the title compound which was used without further purification.

Workup

  1. stirringthe reaction was stirred at RT overnight
  2. customThe reaction was partitioned between water and ethyl acetate
  3. extractionthe aqueous phase was extracted into ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a7e52356adc64f0aa19a092567a99c2e
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08785457B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes