Hydrochloric Acid → HCID 86698487, compound

HRID 403405Notes

Reaction equation

HRID 403405 reaction equation
C(O[C:6](=O)[N:7](C)[C:8]1[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])=[N:10][CH:11]=[N:12][CH:13]=1)(C)(C)C.Cl>O1CCOCC1>[CH3:6][NH:7][C:8]1[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])=[N:10][CH:11]=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86698488HCID 86698488, compound

Product 1

HCID 86698487HCID 86698487, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl-(4-o-tolyl-pyrimidin-5-yl)-carbamic acid tert-butyl ester (120 mg, 0.40 mmol) was treated with 4M HCl in dioxane (3 mL) for 45 minutes after which all volatiles were removed under reduced pressure to give methyl-(4-o-tolyl-pyrimidin-5-yl)-amine as waxy oil. This material was dissolved in dichloromethane (3 mL) and treated with N-ethyldiisopropyl-amine (210 μL, 1.2 mmol) and 3,5-bis-trifluoromethylbenzoyl chloride (166 mg, 0.60 mmol CAS RN 1271-19-8). After stirring for 1 h, the reaction mixture was loaded directly onto a silica gel column. Elution with 50% ethyl acetate in n-hexane yielded the desired compound as a yellow solid (78 mg, 44%). MS (ESI): m/z=440.1 [M+H]+.

Workup

  1. customwere removed under reduced pressure

Sources & evidence

ORD record
ord-677d004676e64b57bf73815e7e2e745c
Source dataset
uspto-grants-2014_06
Patent number
US08748434B2

Reaction notes

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