Acetyl chloride → 1-(2-chloro-4-morpholino-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)ethanone

HRID 1626653Notes

Reaction equation

F[C:2](F)(F)[C:3](O)=[O:4].[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.C(Cl)(=O)C.[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:3](=[O:4])[CH3:2])[CH2:15][C:13]=2[N:14]=1

Participants

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 acetyl chloride (157 uL, 2.2 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 pink solid, which was used without further purification.

Workup

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

Sources & evidence

ORD record: ord-4c41d110a5b647578d855000dbae6023
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785457B2

Reaction notes

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