4-Chloro-2-methylpyridine → HCID 68294290, compound

Participants

Role	Name	HCID	Charge
Reactant	4-Chloro-2-methylpyridine	HCID 581392	—
Reactant	2-AMino-5,8-dihydro-6H-pyrido[3,4-d]pyriMidine-7-carboxylic acid tert-butyl ester	HCID 75487617	—
Reactant	sodium 2-methylpropan-2-olate	HCID 178418730	—
Catalyst	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Solvent	Toluene	HCID 1140	—
Product	HCID 68294290	HCID 68294290	33.2%

Reaction Conditions

Temperature	90 °C

Reaction Steps

A tube was charged with 187 (300 mg, 1.20 mmol), Pd(dba)2 (34.5 mg, 0.0599 mmol), Binap-rac (74.6 mg, 0.120 mmol), 4-chloro-2-methylpyridine (229 mg, 1.80 mmol), and NaO-tert-Bu (230 mg, 2.40 mmol) and toluene (3 mL), sealed, degassed with nitrogen for 5 min then heated to 90° C. for 4 h. The reaction was cooled and filtered through a plug of CELITE®. The filtrate was concentrated and purified by reverse phase column chromatography (SP4) eluting with a MeCN/H2O gradient (5 to 85% MeCN) to afford 136 mg (33.2%) of tert-butyl 2-(2-methylpyridin-4-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate (188).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09133187B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-3ed0b03ef398414faa9e8f2f6eb5b51a
Source note	uspto-grants-2015_09