Potassium Carbonate → 8-(Methoxy)-2-{[2-(methoxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine

HRID 1011027Notes

Reaction equation

FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[NH:11][C:12]2[C:17]([N:18]=1)=[C:16]([NH2:19])[N:15]=[C:14]([O:20][CH2:21][CH2:22][O:23][CH3:24])[N:13]=2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>CN(C=O)C>[CH3:8][O:9][C:10]1[N:11]([CH2:32][CH:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[C:12]2[C:17]([N:18]=1)=[C:16]([NH2:19])[N:15]=[C:14]([O:20][CH2:21][CH2:22][O:23][CH3:24])[N:13]=2

Participants

Conditions

Temperature: 50 °C

Procedure

8-(Methoxy)-2-{[2-(methoxy)ethyl]oxy}-9H-purin-6-amine trifluoroacetate salt (0.30 g) was heated with anhydrous potassium carbonate (0.4698 g) in anhydrous DMF (5 mL) at 60° C. for 1 hour. The reaction mixture was cooled to room temperature before 4-(bromomethyl) tetrahydro-2H-pyran (0.1669 g) was added in anhydrous DMF (1 mL). The reaction mixture was then stirred overnight at 50° C. The reaction mixture was quenched into water (20 mL) and extracted into ethyl acetate (20 mL, 3 times).

Workup

customThe reaction mixture was quenched into water (20 mL)
extractionextracted into ethyl acetate (20 mL, 3 times)

Sources & evidence

ORD record: ord-5d7bf1f56a5d4069823175aedfea47a6
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977344B2

Reaction notes

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