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

HRID 63170Notes

Reaction equation

HRID 63170 reaction equation
[CH3:1][C:2]1[C:3]([NH:17][CH:18]2[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]2)=[N:4][C:5]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[N:6][C:7]=1[CH3:8].Cl>O1CCOCC1>[CH3:1][C:2]1[C:3]([NH:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[N:4][C:5]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[N:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71738920HCID 71738920, compound

Product 1

HCID 717389215,6-dimethyl-N4-(piperidin-4-yl)-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 4-({5,6-dimethyl-2-[(pyridin-2-ylmethyl)amino]pyrimidin-4-yl}amino)piperidine-1-carboxylate (100 mg, 0.24 mmol, Example 82) was suspended in a solution of 3 M hydrogen chloride in dioxane (10 mL). The reaction mixture was stirred at ambient temperature overnight, and then the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel eluted with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1) to afford the titled compound as a light-grey solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.25-1.32 (m, 2H), 1.84-1.92 (m, 5H), 2.25 (s, 3H), 12.43 (bs, 1H), 2.60-2.65 (m, 2H), 3.02-3.08 (m, 2H), 3.985-3.94 (m, 1H), 4.25 (d, J=8.3 Hz, 2H), 4.68 (d, J=5.3 Hz, 2H), 5.59 (bs, 1H), 7.12 (t, J=4.6 Hz, 1H), 7.36 (d, J=8.1 Hz, 1H), 7.60 (t, J=6.4 Hz, 1H), 8.54 (d, J=4.2 Hz, 1H); MS (ESI) m/z 313.2 (M+1)+.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was purified by flash chromatography on silica gel
  3. washeluted with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1)

Sources & evidence

ORD record
ord-f8da1522d927439290b971d05009fb5b
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

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