Anisole → HCID 86663606, compound

HRID 1520744Notes

Reaction equation

HRID 1520744 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]3[CH:18]=[C:17]([NH:19]CC4C=CC(OC)=CC=4)[N:16]=[CH:15][C:11]=3[N:12]=[CH:13][N:14]=2)=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].C1(OC)C=CC=CC=1>C(O)(C(F)(F)F)=O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]3[CH:18]=[C:17]([NH2:19])[N:16]=[CH:15][C:11]=3[N:12]=[CH:13][N:14]=2)=[CH:4][C:3]=1[C:29]([F:30])([F:31])[F:32]

Participants

5

Reactant 2

HCID 7519AnisoleHCID 86663605HCID 86663605, compound

Product 1

HCID 86663606HCID 86663606, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of compound 166 (1.0 g, 2.26 mmol) in TFA (20 mL) was treated with anisole (490 μL, 4.51 mmol) at room temperature. The mixture was stirred overnight, then diluted with ethyl acetate and the solvents were removed under reduced pressure. The residue was triturated with hexane and then treated with aqueous ammonia (5N, 100 mL) with stirring for 30 min. The resulting solid was collected by filtration, washed with water and dried under vacuum to give N4-(4-fluoro-3-(trifluoromethyl)phenyl)pyrido[3,4-d]pyrimidine-4,6-diamine (168) (720 mg, 99%) as a yellow solid, m.p. 252-255° C. 1H NMR [(CD3)2SO] δ 9.90 (s, 1H), 8.72 (s, 1H), 8.38 (s, 1H), 8.34 (dd, J=6.5, 2.6 Hz, 1H), 8.24-8.28 (m, 1H), 7.54 (t, J=9.7 Hz, 1H), 7.14 (s, 1H), 6.30 (s, 2H). Anal. Calcd for C14H9F4N5.0.55EtOAc: C, 52.35; H, 3.63; N, 18.84%. found: C, 51.96; H, 3.70; N, 18.46%.

Workup

  1. customthe solvents were removed under reduced pressure
  2. customThe residue was triturated with hexane
  3. additiontreated with aqueous ammonia (5N, 100 mL)
  4. stirringwith stirring for 30 min
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-067d7973f31046dbb0329f70830a459e
Source dataset
uspto-grants-2015_07
Patent number
US09073916B2

Reaction notes

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