Methyl chloroformate → methyl 2-chloro-4-morpholino-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

HRID 1626655Notes

Reaction equation

HRID 1626655 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.CCN(CC)CC.[CH3:31][O:32][C:33](Cl)=[O:34].[OH-].[Na+]>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:33]([O:32][CH3:31])=[O:34])[CH2:15][C:13]=2[N:14]=1

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 866631634-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)morpholine trifluoroacetate2×

Product 1

HCID 86663169methyl 2-chloro-4-morpholino-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

To a stirring solution of 4-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)morpholine trifluoroacetate (intermediate 20) (2.16 g, 2.0 mmol) in DMF (10 ml), was added Et3N (560 uL, 4.0 mmol). Reaction mixture was stirred at room temperature (20° C.) for 2 minutes followed by the addition of methylchloroformate (186 uL, 2.4 mmol) followed by stirring at room temperature overnight. The reaction mixture was basified (with 2M NaOH) before partitioning between water (25 ml) and DCM (50 ml). The organic layer was recovered, passed through a hydrophobic frit and the solvent removed in vacuo, affording the title compound as a brown solid used without further purification.

Workup

  1. customReaction mixture
  2. stirringby stirring at room temperature overnight
  3. custombefore partitioning between water (25 ml) and DCM (50 ml)
  4. customThe organic layer was recovered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-43855ddbb17246edba0d1364d4cc62dd
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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