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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1295659Generated: November 1, 2026

Thionyl Chloride → Benzo[1,3]dioxol-5-yl-[6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine

https://huagongshe.com/reaction/1295659

Reaction equation

Participants

RoleNameHCIDCharge
ReactantThionyl ChlorideHCID 24386—
Reactant{4-[4-(Benzo[1,3]dioxol-5-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanolHCID 69180666—
SolventEthyl AcetateHCID 8857—
SolventSodium BicarbonateHCID 516892—
SolventAcetonitrile dioxaneHCID 22504236—
ProductBenzo[1,3]dioxol-5-yl-[6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amineHCID 69179724—

Reaction Steps

To a suspension of 1.83 g of {4-[4-(benzo[1,3]dioxol-5-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl ]-phenyl}-methanol in 56 ml of dioxane/acetonitrile 1:1 under N2-atmosphere, 3.1 ml of thionylchloride are added. After 16 h stirring, the suspension is diluted with ethyl acetate and NaHCO3-solution. The aqueous layer is separated off and extracted twice with ethyl acetate. The organic phases are washed with water and brine, dried (MgSO4) and concentrated to yield the title compound; MS-ES+: (M+H)+=379; HPLC (conditions see Examples 67-78) tR=11.4 min.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07244729B2
Source datasetuspto-grants-2007_07
ORD IDord-389dffea57284d1f9fab75140dcb121e
Source noteuspto-grants-2007_07