Diisopropylethylamine → (+/-)-N4-(3,4-difluorophenyl)-5-fluoro-N2-[2,3-dihydro-2-(N-methylamino)carbonylbenzofuran-5-yl]-2,4-pyrimidinediamine

HRID 1753597Notes

Reaction equation

HRID 1753597 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]([F:16])=[CH:14][N:13]=[C:12]([NH:17][C:18]3[CH:19]=[CH:20][C:21]4[O:25][CH:24]([C:26]([O:28]C)=O)[CH2:23][C:22]=4[CH:30]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].Cl.CN.[CH:34]([N:37](C(C)C)CC)(C)C>CO.O>[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]([F:16])=[CH:14][N:13]=[C:12]([NH:17][C:18]3[CH:19]=[CH:20][C:21]4[O:25][CH:24]([C:26]([NH:37][CH3:34])=[O:28])[CH2:23][C:22]=4[CH:30]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 22060930(+)-N4-(3,4-difluorophenyl)-N2-(2,3-dihydro-2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine

Product 1

HCID 22060649(+/-)-N4-(3,4-difluorophenyl)-5-fluoro-N2-[2,3-dihydro-2-(N-methylamino)carbonylbenzofuran-5-yl]-2,4-pyrimidinediamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (±)-N4-(3,4-difluorophenyl)-N2-(2,3-dihydro-2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine, methylamine Hydrogen Chloride (5 equivalents) and diisopropylethylamine (5 equivalents) in MeOH was shaken in a sealed tube at 80° C. for 24 h. The resulting solution was diluted with water and the precipitate obtained was filtered, washed with water, dried and analyzed to afford (±)-N4-(3,4-difluorophenyl)-5-fluoro-N2-[2,3-dihydro-2-(N-methylamino)carbonylbenzofuran-5-yl]-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.46 (s, 1H), 9.07 (s, 1H), 8.05 (m, 3H), 7.48 (m, 2H), 7.35 (m, 1H), 7.22 (m, 1H), 6.72 (d, 1H, J=8.1 Hz), 5.07 (dd, 1H, J=6.6 and 6.3 Hz), 3.40 (dd, 1H), 3.15 (dd, 1H), 2.60 (d, 3H, J=4.5 Hz); LCMS: purity: 98%; MS (m/e): 416 (MH+).

Workup

  1. customthe precipitate obtained
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-71b70ada33194dacac7bf141d5f26e66
Source dataset
uspto-grants-2015_10
Patent number
US09162989B2

Reaction notes

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