Ethyl acetate hexane → HCID 86724339, compound

HRID 2274266Notes

Reaction equation

HRID 2274266 reaction equation
[F:1][C:2]1[C:3]([NH:21][C:22]2[CH:23]=[C:24]([NH:28]C(=O)OC(C)(C)C)[CH:25]=[CH:26][CH:27]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:11]([OH:20])[CH:10]=2)=[N:6][CH:7]=1.C(OCC)(=O)C.CCCCCC>C(Cl)Cl>[NH2:28][C:24]1[CH:23]=[C:22]([NH:21][C:3]2[C:2]([F:1])=[CH:7][N:6]=[C:5]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:11]([OH:20])[CH:10]=3)[N:4]=2)[CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 86724338Tert-butyl (3-((5-fluoro-2-((3-hydroxy-4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)carbamate

Product 1

HCID 86724339HCID 86724339, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl (3-((5-fluoro-2-((3-hydroxy-4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)carbamate (0.240 g) in DCM (5.0 mL) TFA (2.0 mL) was added at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes followed by stirring at room temperature for 30 minutes. The reaction was monitored by TLC using ethyl acetate:hexane (7:3) as mobile phase. After completion of the reaction, the mixture was quenched in water and basified with saturated sodium bicarbonate solution. Product was extracted into DCM. The organic layer was washed with brine and dried over sodium sulfate and concentrated completely under reduce pressure at 40° C. The obtained solid was purified by trituration with ether to give 0.175 g of 5-((4-((3-aminophenyl)amino)-5-fluoropyrimidin-2-yl)amino)-2-(2-methoxyethoxy)phenol. 1H NMR: DMSO-d6 (400 MHz): 3.282 (s, 3H), 3.617-3.640 (t, 2H, J=4.4), 4.004-4.040 (t, 2H, J=4.4), 4.992 (s, 2H), 6.306-6.316 (d, 1H, J=3.2), 6.772-6.793 (d, 1H, J=8.4), 6.952-7.042 (m, 3H), 7.095 (s, 1H), 7.187 (s, 1H), 8.004-8.013 (d, 1H, J=3.6), 8.811 (s, 1H), 8.861 (s, 1H), 9.001 (s, 1H).

Workup

  1. stirringby stirring at room temperature for 30 minutes
  2. customAfter completion of the reaction
  3. customthe mixture was quenched in water and basified with saturated sodium bicarbonate solution
  4. extractionProduct was extracted into DCM
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated completely
  8. customat 40° C
  9. customThe obtained solid was purified by trituration with ether

Sources & evidence

ORD record
ord-d23574dc45634999ad6400ef7aaea94c
Source dataset
uspto-grants-2015_09
Patent number
US09126950B2

Reaction notes

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