Hydrochloric Acid → N4-cyclohexyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine hydrochloride

HRID 63096Notes

Reaction equation

HRID 63096 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:5]([CH3:15])=[C:4]([CH3:16])[N:3]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][NH2:24].Cl>C(#N)C.O1CCOCC1>[ClH:1].[CH:9]1([NH:8][C:6]2[C:5]([CH3:15])=[C:4]([CH3:16])[N:3]=[C:2]([NH:24][CH2:23][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][N:17]=3)[N:7]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 195092-PyridinemethanamineHCID 824606262-chloro-N-cyclohexyl-5,6-dimethylpyrimidin-4-amine

Product 1

HCID 131737202N4-cyclohexyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine hydrochlorideYield 50.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-chloro-N-cyclohexyl-5,6-dimethylpyrimidin-4-amine (0.1 g, 0.40 mmol) and (pyridin-2-ylmethyl)amine (0.04 g, 0.400 mmol) in acetonitrile (5 mL) was added a 3.5 M solution of hydrogen chloride in dioxane (0.2 mL). The resulting mixture was irradiated in CEM Focused Microwave™ Synthesis System at 160° C. for 120 minutes. The resulting mixture was cooled to ambient temperature. The formed precipitate was collected by filtration and dried to yield 0.07 g (48.2%) of the titled compound as the hydrochloride salt. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.99-1.03 (m, 2H), 1.13 (d, J=12.63 Hz, 1H), 1.20-1.26 (m, 2H), 1.51-1.59 (m, 2H), 1.60-1.63 (m, 3H), 1.89 (s, 3H), 2.24 (s, 3H), 3.70 (s, 1H), 4.62 (d, J=5.10 Hz, 2H), 7.24 (dd, J=7.25, 4.84 Hz, 1H), 7.31 (d, J=7.79 Hz, 1H), 7.58 (d, J=7.72 Hz, 1H, 7.74 (t, J=7.66 Hz, 1H), 8.1 (s, 1H), 8.50 (d, J=4.84 Hz, 1H); MS (ESI) m/z 312.3 (M+1)+.

Workup

  1. customThe resulting mixture was irradiated in CEM Focused Microwave™ Synthesis System at 160° C. for 120 minutes
  2. filtrationThe formed precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-6e207b14d4574eb89922e20d5cf7017e
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

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