Hydrochloric Acid → HCID 22048124, compound

HRID 1830582Notes

Reaction equation

HRID 1830582 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.Cl.[NH:11]([C:18]1[C:23]([Br:24])=[CH:22][N:21]=[C:20](Cl)[N:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)CCC>[NH:11]([C:18]1[C:23]([Br:24])=[CH:22][N:21]=[C:20]([NH:1][C:2]2[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=2)[N:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4278144-AminobenzylamineHCID 114033895-bromo-2-chloro-N-phenylpyrimidin-4-amine

Product 1

HCID 22048124HCID 22048124, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

4-Aminobenzylamine (122 mg, 1.0 mmol) and ethereal hydrogen chloride (1.0 M; 1.0 ml, 1.0 mmol) were added to a solution of 4-anilino-5-bromo-2-chloropyrimidine (256 mg, 0.9 mmol) in n-butanol (4 ml) and the mixture was heated at 100° C. for 16 hours. The insoluble solid was filtered off and dissolved in methanol (5 ml). Silica (2 g) was added and volatile material was removed by evaporation. The residue was purified by bond elute chromatography, eluting with 0–4% 2.0 M methanolic ammonia solution in DCM, to give the product (163 mg, 49%): LCMS (MH+): 370, 372; HPLC (RT, System A): 2.04.

Workup

  1. filtrationThe insoluble solid was filtered off
  2. dissolutiondissolved in methanol (5 ml)
  3. additionSilica (2 g) was added
  4. customvolatile material was removed by evaporation
  5. customThe residue was purified by bond
  6. washelute chromatography
  7. washeluting with 0–4% 2.0 M methanolic ammonia solution in DCM

Sources & evidence

ORD record
ord-5bc25950f4e547edb7f74e29ee4cac60
Source dataset
uspto-grants-2006_06
Patent number
US07067522B2

Reaction notes

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