HCID 22060606, compound → HCID 22060522, compound

HRID 1724264Notes

Reaction equation

HRID 1724264 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-0e1835eb038d4f309e0b17d69ff5b5a5
Source dataset
uspto-grants-2009_02
Patent number
US07485724B2

Reaction notes

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