tert-Butyl carbamate → tert-Butyl (5-(pyrimidin-5-yloxy)pyridin-3-yl)carbamate

Participants

Role	Name	HCID	Charge
Reactant	tert-Butyl carbamate	HCID 77922	—
Reactant	Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane	HCID 11618717	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	5-((5-Bromopyridin-3-yl)oxy)pyrimidine	HCID 51037932	—
Catalyst	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Solvent	Toluene	HCID 1140	—
Product	tert-Butyl (5-(pyrimidin-5-yloxy)pyridin-3-yl)carbamate	HCID 58349145	100%

Reaction Steps

Compound 5 (1.0 g, 4.0 mmol, 1.0 eq), tert-Butyl carbamate (560 mg, 4.78 mmol, 1.20 eq), tris(dibenzylideneacetone) dipalladium-chloroform adduct (120 mg, 0.116 mmol, 0.0300 eq), sodium tert-butoxide (530 mg, 5.52 mmol, 1.40 eq), and 2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (180 mg, 0.424 mmol, 0.0900 eq) stirred in toluene (15 mL) at rt overnight. The mixture was filtered through celite and washed with 5% MeOH in CH2Cl2. The filtrate was collected and concentrated in vacuo to afford 1.1 g (100%) of the title compound as an orange solid: 1H NMR (400 MHz, DMSO-d6) δ 9.79 (s, 1H), 9.05 (s, 1H), 8.72 (s, 2H), 8.45 (d, J=1.7 Hz, 1H), 8.10 (t, J=2.5 Hz, 1H), 7.69 (s, 1H), 1.45 (s, 9H); ES-MS [M+1]+: 289.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08569308B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-00c9530691ef40e79b612811f91bc504
Source note	uspto-grants-2013_10