HCID 22060606, compound → HCID 22060522, compound

HRID 528095Notes

Reaction equation

HRID 528095 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][N:15](C(OC(C)(C)C)=O)[CH2:16]3)=[CH:11][CH:10]=2)[C:5]([F:26])=[CH:4][N:3]=1>FC(F)(F)C(O)=O.ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][NH:15][CH2:16]3)=[CH:11][CH:10]=2)[C:5]([F:26])=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 22060606HCID 22060606, compound

Product 1

HCID 22060522HCID 22060522, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 2-chloro-5-fluoro-N4-[2-(t-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]-4-pyrimidineamine in 40% trifluoroacetic acid/dichloromethane was stirred at rt for 30 min. Removal of the solvent left an oily residue which was suspended in water, made basic with NaHCO3, and extracted with ethyl acetate. Purification by column chromatography over silica gel provided 2-chloro-5-fluoro-N4-(1,2,3,4-tetrahydroisoquinolin-7-yl)-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.04 (d, 1H, J=3.0 Hz), 7.37 (dd, 1H, J=2.4 and 8.4 Hz), 7.27 (d, 1H, J=1.5 Hz), 7.11 (d, 1H, J=8.4 Hz), 6.92 (s, 1H), 4.04 (s, 2H), 3.15 (t, 2H, J=6.0 Hz), 2.79 (t, 2H, J=6.0 Hz); 19F NMR (282 MHz, CDCl3): −44648; LCMS: purity: 97%; MS (m/e): 279 (MH+).

Workup

  1. customRemoval of the solvent
  2. waitleft an oily residue which
  3. extractionextracted with ethyl acetate
  4. customPurification by column chromatography over silica gel

Sources & evidence

ORD record
ord-dfc82c2491964e91bce2f5df0c06b9c7
Source dataset
uspto-grants-2016_05
Patent number
US09346765B2

Reaction notes

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