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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1876491Generated: October 31, 2026

Sodium Carbonate → 5-[9-(Cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]pyrimidin-2-amine

https://huagongshe.com/reaction/1876491

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant1,4-DioxaneHCID 31275—
Reactant2-Aminopyrimidine-5-boronic acid, pinacol esterHCID 17750212—
Reactant2-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purineHCID 59333552—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
Product5-[9-(Cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]pyrimidin-2-amineHCID 59333575101%

Reaction Steps

Sodium carbonate (3.25 g, 30.6 mmol) and tetrakis triphenylphosphine palladium (0.59 g, 0.51 mmol) were added to a 1,4-dioxane (60.0 ml)-water (30.0 ml) mixture solution of 2-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purine (3.0 g, 10.2 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (2.5 g, 11.2 mmol) at room temperature and the resulting mixture was heated to reflux for 3 hours in an argon atmosphere. The reaction mixture was left standing to cool and then poured into water, and ethyl acetate was added to separate the layers. The solid precipitated in the aqueous layer was collected by filtration, washed with water, and dried at 50° C. under reduced pressure to give the title compound (3.63 g, 100%) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08309546B2
Source datasetuspto-grants-2012_11
ORD IDord-d361f3bab9a64d59bcc37714e846dd2f
Source noteuspto-grants-2012_11