Methanol → HCID 23295689, compound

HRID 1953969Notes

Reaction equation

HRID 1953969 reaction equation
Cl[C:2]1[C:7]([CH2:8][CH3:9])=[C:6]([O:10][C:11]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[S:13][CH:12]=2)[N:5]=[C:4]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[N:3]=1.CO.C(N(CC)CC)C>[Pd].C(OCC)(=O)C>[CH2:8]([C:7]1[CH:2]=[N:3][C:4]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[N:5][C:6]=1[O:10][C:11]1[CH:15]=[C:14]([C:16]([F:17])([F:19])[F:18])[S:13][CH:12]=1)[CH3:9]

Participants

6

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 15477078HCID 15477078, compound

Product 1

HCID 23295689HCID 23295689, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-Chloro-5-ethyl-2-(α,α,α-trifluoro-p-tolyl)-6-{[5-(trifluoromethyl)-3-thienyl]oxy}pyrimidine (1.06 g, 2.34 mmol) in a 1:1 mixture of methanol:ethyl acetate is treated with triethylamine (0.80 ml, 5.86 mmol) and 10% Pd-C (0.32 g, 30 wt %). The resultant mixture is placed on a PARR hydrogenator at 50 psi for 2 hours (reaction is complete by TLC). The resultant mixture is filtered. The filtrate is concentrated. The 20/80) to give the title product as a white solid, 0.69 9 (70%), mp 67-68° C. identified by 1HNMR, 13CNMR, 19FNMR, mass spectral and elemental analyses.

Workup

  1. custom(reaction is complete by TLC)
  2. filtrationThe resultant mixture is filtered
  3. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-0770a3b880004a8b8ad13ac1acd04ba7
Source dataset
uspto-grants-2000_09
Patent number
US06121202

Reaction notes

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