Ethyl chloroformate → HCID 86663155, compound

HRID 1626573Notes

Reaction equation

HRID 1626573 reaction equation
Cl.[Cl:2][C:3]1[N:4]=[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[C:6]2[CH2:11][NH:10][CH2:9][C:7]=2[N:8]=1.Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21].C([O-])(O)=O.[Na+]>C1COCC1>[Cl:2][C:3]1[N:4]=[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[C:6]2[CH2:11][N:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:9][C:7]=2[N:8]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 86663150(S)-4-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine hydrochloride2×

Product 1

HCID 86663155HCID 86663155, compoundYield 112.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-4-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine hydrochloride (intermediate 6) (330 mg, 1.3 mmol), was dissolved in dry THF with srirring and treated with ethyl chloroformate (136 uL, 1.4 mmol) and NaHCO3 (218 mg, 2.6 mmol) at room temperature (20° C.) overnight. The mixture was concentrated in vacuo and the residue purified by flash chromatography using a mixture of 0-100% petrol ether/ethyl acetate as eluent, yielding the title compound (475 mg, 1.46 mmol, 41%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue purified by flash chromatography
  3. additiona mixture of 0-100% petrol ether/ethyl acetate as eluent

Sources & evidence

ORD record
ord-1a1589f3524742e4b53365bdfa546d2c
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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