Hydrochloric Acid → HCID 67202054, compound

HRID 547550Notes

Reaction equation

HRID 547550 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[NH2:11][C:12]1[N:17]=[C:16]([CH3:18])[CH:15]=[C:14]([Cl:19])[N:13]=1.Cl>C(OCCO)C>[ClH:19].[NH2:11][C:12]1[N:13]=[C:14]([NH:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH:15]=[C:16]([CH3:18])[N:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9784-Aminobenzoic AcidHCID 218102-Amino-4-chloro-6-methylpyrimidine

Product 1

HCID 67202054HCID 67202054, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
20 °C

Procedure

p-Aminobenzoic acid (D1) (1.48 g, 10.8 mmol) and 4-chloro-6-methyl-2-pyrimidinamine (A8) (1.60 g, 11.9 mmol) was dissolved in warm 2-ethoxyethanol (20 mL),then two drops of c.HCl was added and refluxed for 1 h. The reaction mixture was cooled to 20° C. and the resulting precipitate was filtered washed with more 2-ethoxyethanol and EtOAc. The solid was boiled in MeOH, cooled and filtered washed with more MeOH and dried to give D2 (2.89 g, 95%); m.p. (MeOH)>300° C.; 1H NMR [(CD3)2SO] δ12.93 (br, 1 H, N+H or COOH), 12.80 (br, 1 H, N+H or COOH), 10.87 (s, 1 H, NH), 7.92 (s, 6 H, ArH &NH2)), 6.27 (s, 1 H, ArH), 2.32 (s, 3 H, CH3); mass APCI+ 245.

Workup

  1. temperaturerefluxed for 1 h
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with more 2-ethoxyethanol and EtOAc
  4. temperaturecooled
  5. filtrationfiltered
  6. washwashed with more MeOH
  7. customdried

Sources & evidence

ORD record
ord-1c862c9aa8e9488ab8c39af82f26aa42
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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