tert-Butyl carbamate → (4-Hydroxymethyl-6-methyl-pyridine-2-yl)-carbamic acid tert-butyl ester

HRID 676Notes

Reaction equation

HRID 676 reaction equation
CC(C)(C)OC(N)=O.Cc1cc(CO)cc(Cl)n1>C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>Cc1cc(CO)cc(NC(=O)OC(C)(C)C)n1

Participants

7

Reactant 2

HCID 77922tert-Butyl carbamateHCID 22504306(2-Chloro-6-methylpyridin-4-yl)methanol

Product 1

HCID 57446746(4-Hydroxymethyl-6-methyl-pyridine-2-yl)-carbamic acid tert-butyl esterYield 0%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A 2.0-5.0 mL microwave vial was charged with XANTPHOS (14.66 mg, 0.03 mmol), Pd2(dba)3 (29.1 mg, 0.03 mmol), CESIUM CARBONATE (155 mg, 0.48 mmol),(2-chloro-6-methylpyridin-4-yl)methanol (50 mg, 0.32 mmol), tert-butyl carbamate (44.6 mg, 0.38 mmol) and dioxane (3 mL). The reaction mixture was degassed for 2 minutes with nitrogen, and then the reaction mixture was stirred at 80°C under microwave irradiation for 30 min. Water (5 mL) was added and the mixture was washed using EtOAc (3 x 10 mL). The organic layers were combined, dried using MgSO4, filtered and concentrated. The crude material was loaded on a 12g silica gel column and purified on a Teledyne Isco instrument, eluting with 0% to 20% EtOAc in DCM. The product that seems to be the compound was collected. Unfrtunately NMR showed that this compound is dba. The compound was not isolated.

Sources & evidence

ORD record
ord-4ba8493a4d7f4107b8a89b01cdd11168
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

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