Hydrochloric Acid → HCID 9903129, compound

HRID 1765307Notes

Reaction equation

HRID 1765307 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[NH:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:10]=[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[N:8]=1.Cl>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[NH:6][C:7]1[CH:12]=[C:11]([C:13]([F:14])([F:16])[F:15])[N:10]=[C:9]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][NH:18]2)[N:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 9950111HCID 9950111, compound

Product 1

HCID 9903129HCID 9903129, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(3-methoxyanilino)-2-(2-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.144 mmol) in methanol (20 ml) was added concentrated hydrochloric acid (200 ul). The mixture was hydrogenated over palladium (5 wt % on activated carbon) at 50 psi for 6 h. The mixture was filtered through Celite. The filtrate was rotary evaporated to dryness and purified by column chromatography to give a brown oil (3 mg, 6%). 1H NMR (CDCl3): 7.83 (s, 1H), 7.31 (d, J=7.8 Hz, 1H), 6.90–6.85 (m, 3H), 6.77 (dd, J=1.8, 7.8 Hz, 1H), 3.90 (dd, J=3.0, 10.5 Hz, 1H), 3.81 (s, 3H), 3.29 (d, J=11.4 Hz, 1H), 2.88–2.80 (m, 2H), 2.25 (d, J=10.5 Hz, 1H), 1.92 (s, 1H), 1.69–1.56 (m, 4H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customThe filtrate was rotary evaporated to dryness
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-c3b9216b2c5d4005987c4bab75d0d5dc
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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