Hydrochloric Acid → 6-(4-Amino-2-fluorophenoxy)pyrimidin-4-amine

HRID 2373954Notes

Reaction equation

HRID 2373954 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15]C(=O)C)=[CH:11][C:10]=2[F:19])[CH:3]=1.Cl.C([O-])([O-])=O.[Na+].[Na+]>CO>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[CH:3]=2)=[C:10]([F:19])[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 59852900N-(4-(6-aminopyrimidin-4-yloxy)-3-fluorophenyl)acetamide

Product 1

HCID 598528916-(4-Amino-2-fluorophenoxy)pyrimidin-4-amineYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(4-(6-aminopyrimidin-4-yloxy)-3-fluorophenyl)acetamide (175 mg, 0.67 mmol), 1 M HCl (6 mL), and MeOH (2 mL) was heated at reflux for 3 h. The reaction mixture was cooled, made basic (pH 8) with aqueous Na2CO3 solution and extracted with EtOAc (2×25 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to give the title compound (140 mg, 96%) as a brown solid. 1H NMR (DMSO-d6) δ 8.02 (s, 1H), 6.89 (dd, 1H, J=9.0, 9.0 Hz), 6.80 (br s, 2H), 6.43 (dd, 1H, J=12.7, 2.8 Hz), 6.35 (dd, 1H, J=8.8, 2.2 Hz), 5.67 (s, 1H), 5.34 (br s, 2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with EtOAc (2×25 mL)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-19bdf70981f64b32bc01d7ddcf985c1b
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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