Triphenylphosphine → 1,1-Dimethylethyl 4-({[2-(4-bromophenyl)-5-pyrimidinyl]oxy}methyl)-1-piperidinecarboxylate

Participants

Role	Name	HCID	Charge
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	Diisopropyl diazene-1,2-dicarboxylate	HCID 75555	—
Reactant	2-(4-Bromophenyl)pyrimidin-5-ol	HCID 619908	—
Reactant	Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate	HCID 2764081	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	1,1-Dimethylethyl 4-({[2-(4-bromophenyl)-5-pyrimidinyl]oxy}methyl)-1-piperidinecarboxylate	HCID 66673116	—

Reaction Steps

1,1-Dimethylethyl 4-({[2-(4-bromophenyl)-5-pyrimidinyl]oxy}methyl)-1-piperidinecarboxylate was prepared (0.387 g, 76%) as a white solid from 2-(4-bromophenyl)-pyrimidine-5-ol (0.30 g, 1.19 mmol), N-Boc-4-piperidinemethanol (0.27 g, 1.19 mmol) and Ph3P (0.32 g, 1.19 mmol) in THF (8 mL) followed by diisopropyl azodicarboxylate (0.26 g, 94%, 1.19 mmol) in THF (3 mL) in a manner similar to Example 1, Step 2. 1H NMR (400 MHz, CDCl3): δ 8.44 (s, 2H), 8.22 (d, 2H, J=8.3 Hz), 7.59 (d, 2H, J=8.3 Hz), 4.25-4.10 (m, 2H), 3.94 (d, 2H, J=6.1 Hz), 2.85-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.46 (s, 9H), 1.35-1.20 (m, 2H); LRMS (ESI), m/z 448/450 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08101634B2
Source dataset	uspto-grants-2012_01
ORD ID	ord-131a37b696e642708fd1ae02d3e1e94b
Source note	uspto-grants-2012_01