Sulfuric Acid → HCID 11544227, compound

HRID 628823Notes

Reaction equation

HRID 628823 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]([C:16]3[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=3)[C:19]#[N:20])[CH:13]=[CH:12][N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[OH:24]S(O)(=O)=O.[OH-].[Na+]>>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:15]=[C:14]([C:16]3[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=3)[C:19]([NH2:20])=[O:24])[CH:13]=[CH:12][N:11]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 69235511HCID 69235511, compound

Product 1

HCID 11544227HCID 11544227, compoundYield 98%

Conditions

Temperature
70 °C

Procedure

A mixture of 3-[2-(4-isopropyl-phenyl)-pyrimidin-4-yl]-benzonitrile (50 mg, 0.167 mmol) and aq. H2SO4 (257 μL, 0.65 M) is heated to 70° C. for 12 h. The mixture is cooled and adjusted to pH 7 with aq. sodium hydroxide (1 M). The mixture is partitioned between water and ethyl acetate, and the organic layer is washed with satd. aq. sodium chloride solution, dried over magnesium sulfate, filtered and evaporated to afford the title compound as a white crystalline solid (52 mg, 98%), m.p. 167-169° C. 1H NMR (300 MHz, acetone-d6): δ 8.91 (1H, d, J=6 Hz), 8.87 (1H, t, J=2 Hz), 8.54 (2H, d, J=9 Hz), 8.52 (1H, ddd, J=8, 2, 1 Hz), 8.15 (1H, ddd, J=8, 2, 1 Hz), 7.93 (1H, d, J=6 Hz), 7.80 (1H, br s), 7.68 (1H, t, J=8 Hz), 7.41 (2H, d, J=9 Hz), 6.96 (1H, br s), 3.01 (1H, heptet, J=7 Hz), 1.30 (6H, d, J=7 Hz). 13C NMR (acetone-d6): δ 205.9, 168.4, 164.8, 163.4, 159.0, 152.4, 137.8, 136.2, 135.9, 130.6 (2C), 129.7, 128.9, 127.2 (2C), 126.8, 115.4, 34.7, 24.1 (2C). MS (ES+): m/e 319 (25), 318 (100).

Workup

  1. temperatureThe mixture is cooled
  2. customThe mixture is partitioned between water and ethyl acetate
  3. washthe organic layer is washed with satd
  4. dry with materialaq. sodium chloride solution, dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e33b1fd9d1ba475fa56c21a9985f7f2c
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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