Chlorotrimethylsilane → 6-(2-(1H-indazol-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one

Participants

Role	Name	HCID	Charge
Reactant	Chlorotrimethylsilane	HCID 6397	—
Reactant	1H-Indazol-6-amine	HCID 81423	—
Reactant	6-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one	HCID 86628038	—
Solvent	1-Butanol	HCID 263	—
Product	6-(2-(1H-indazol-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one	HCID 25196013	6.2%

Reaction Conditions

Temperature	115 °C

Reaction Steps

To a mixture of 6-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one (0.050 g) inn-butyl alcohol (0.6 mL) was added 6-aminoindazole (0.028 g) and trimethylsilyl chloride (TMSCl) (0.013 mL). After heating at 115° C. for 15 h, the mixture was purified by preparative HPLC to give 6-(2-(1H-indazol-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one (0.004 g, MS [MH] 441.1) (Compound 16-1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07705004B2
Source dataset	uspto-grants-2010_04
ORD ID	ord-58013d8bb578455dbc65aaca5e1fd0e3
Source note	uspto-grants-2010_04