Cesium carbonate → tert-Butyl-6-(((1S,2S)-2-(5-(2-hydroxypropan-2-yl)pyridin-2-yl)cyclopropyl)methoxy)-2-methylpyrimidin-4-yl((5-methyl-1,3,4-thiadiazol-2-yl)methyl)carbamate

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Binap, (A+-)-	HCID 634876	—
Reactant	Tert-butyl ((5-methyl-1,3,4-thiadiazol-2-yl)methyl)carbamate	HCID 59892191	—
Reactant	2-(6-((1S,2S)-2-((6-chloro-2-methylpyrimidin-4-yloxy)methyl)cyclopropyl)pyridin-3-yl)propan-2-ol	HCID 86729574	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Toluene	HCID 1140	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	tert-Butyl-6-(((1S,2S)-2-(5-(2-hydroxypropan-2-yl)pyridin-2-yl)cyclopropyl)methoxy)-2-methylpyrimidin-4-yl((5-methyl-1,3,4-thiadiazol-2-yl)methyl)carbamate	HCID 90332200	99.2%

Reaction Conditions

Temperature	85 °C

Reaction Steps

The mixture of 8-3 (60 mg, 0.18 mmol), 8-4 (50 mg, 0.22 mmol), Cs2CO3 (88 mg, 0.27 mmol), Pd(OAc)2 (8.1 mg, 0.036 mmol), BINAP (25 mg, 0.040 mmol) in toluene (2.0 mL) was heated at 85° C. for overnight. Then the reaction mixture was diluted with EtOAc (20 mL), filtered and concentrated in vacuo to give crude product (94 mg) which was used for next step without further purification. LRMS (ES) calculated M+H for C26H34N6O4S: 527.24. Found: 527.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09062059B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-129b659238bb44ecbe90d2caf4204167
Source note	uspto-grants-2015_06