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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1666078Generated: October 30, 2026

Diisopropylethylamine → 3-[5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-(pyrrolidin-3-ylamino)-pyrimidin-4-ylamino]-N-methoxy-4-methyl-benzamide

https://huagongshe.com/reaction/1666078

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactant(R)-(+)-1-Boc-3-aminopyrrolidineHCID 854070—
Reactant3-{5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-methanesulfinyl-pyrimidin-4-ylamino}-N-methoxy-4-methyl-benzamideHCID 58928503—
Solvent1,4-DioxaneHCID 31275—
Product3-[5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-(pyrrolidin-3-ylamino)-pyrimidin-4-ylamino]-N-methoxy-4-methyl-benzamideHCID 72465904—

Reaction Steps

3-{5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-methanesulfinyl-pyrimidin-4-ylamino}-N-methoxy-4-methyl-benzamide (33 mg) and 1-N-Boc-3-(R)-aminopyrrolidine (30 mg), DIEA (0.2 mL) and p-dioxane (2 mL) were heated in a sealed tube at 75° C. for overnight. After the removal of the solvent in vacuo, the product was purified by silica gel column chromatography and treated with TFA/DCM (1:1) in order to remove the Boc-group. The product was then converted to hydrochloride salt by treating it with hydrochloric acid (1 M in ether) (Yield: 20 mg). MS (m/z): 567 (M+H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08044040B2
Source datasetuspto-grants-2011_10
ORD IDord-90cad3a4b61d43e7bf4e82c11aa5395c
Source noteuspto-grants-2011_10