Triethylamine → Ethyl 4-(5-(4-(4-methoxybenzyloxy)-2-(pyridin-2-yl)pyrimidin-5-yl)isoxazol-3-yl)phenyl(methyl)phosphinate

HRID 1525345Notes

Reaction equation

HRID 1525345 reaction equation
Cl/[C:2](=[N:15]\[OH:16])/[C:3]1[CH:8]=[CH:7][C:6]([P:9]([CH3:14])(=[O:13])[O:10][CH2:11][CH3:12])=[CH:5][CH:4]=1.[C:17]([C:19]1[C:20]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)=[N:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)=[N:23][CH:24]=1)#[CH:18].C(N(CC)CC)C>C1COCC1>[CH3:40][O:39][C:36]1[CH:35]=[CH:34][C:33]([CH2:32][O:31][C:20]2[C:19]([C:17]3[O:16][N:15]=[C:2]([C:3]4[CH:8]=[CH:7][C:6]([P:9]([CH3:14])(=[O:13])[O:10][CH2:11][CH3:12])=[CH:5][CH:4]=4)[CH:18]=3)=[CH:24][N:23]=[C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[N:21]=2)=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 894627915-Ethynyl-4-(4-methoxybenzyloxy)-2-(pyridin-2-yl)pyrimidineHCID 89470837(1Z)-4-[ethoxy(methyl)phosphoryl]-N-hydroxybenzenecarboximidoyl chloride

Product 1

HCID 89462877Ethyl 4-(5-(4-(4-methoxybenzyloxy)-2-(pyridin-2-yl)pyrimidin-5-yl)isoxazol-3-yl)phenyl(methyl)phosphinateYield 55.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of compound 38-e (750 mg, 2.8 mmol), compound 37-j (820 mg, 2.6 mmol) and triethylamine (780 mg, 7.8 mmol) in THF (20 mL) was stirred at room temperature for 12 h. The resulting mixture was concentrated under reduce pressure, purified by column chromatography on silica gel (DCM:MeOH=30:1) to give compound 38-f (780 mg). LC-MS 543 [M+H]+

Workup

  1. concentrationThe resulting mixture was concentrated
  2. custompurified by column chromatography on silica gel (DCM:MeOH=30:1)

Sources & evidence

ORD record
ord-8f8afb4fc5d14e648ba032f0f43b34bc
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

Loading…