Hydrochloric Acid → 2-Anilinopyrimidine-4-carbaldehyde

HRID 2105127Notes

Reaction equation

HRID 2105127 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]([CH:14](OC)[O:15]C)[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>>[NH:1]([C:8]1[N:13]=[C:12]([CH:14]=[O:15])[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 57807799HCID 57807799, compound

Product 1

HCID 578078012-Anilinopyrimidine-4-carbaldehydeYield 78%

Conditions

Temperature
50 °C

Procedure

A mixture of 2-anilino-4-(dimethoxymethyl)pyrimidine (Method 2; 26.5 g, 0.108 mol) and 3M hydrochloric acid (108 ml, 0.324 mol) was stirred and heated at 50° C. for 18 hours. The reaction mixture was allowed to cool and the pH of the solution adjusted to 9 by careful addition of solid sodium carbonate. The mixture was extracted with EtOAc (5×100 ml). The combined extracts were washed with water (2×100 ml), dried (Na2SO4) and evaporated to give the title compound (16.2 g, 78%) as a brown solid. NMR: (CDCl3): 7.10 (t, 1H), 7.20 (d, 1H), 7.40 (t, 3H), 7.68 (d, 21), 8.64 (d, 1H), 9.90 (s, 1H), m/z 232 [MH+MeOH]+.

Workup

  1. temperatureto cool
  2. extractionThe mixture was extracted with EtOAc (5×100 ml)
  3. washThe combined extracts were washed with water (2×100 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-d0a773bde8184791b52084e5ad10e172
Source dataset
uspto-grants-2009_08
Patent number
US07579344B2

Reaction notes

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