Diisopropylethylamine → HCID 118023134, compound

HRID 522646Notes

Reaction equation

HRID 522646 reaction equation
[CH2:1]([C:8]1[CH:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[N:25]=[C:24](Cl)[N:23]=[CH:22][N:21]=3)[CH2:16][CH2:15]2)=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][C:28]1([CH3:40])[O:32][CH:31]([CH2:33][N:34]2[CH:38]=[C:37]([NH2:39])[CH:36]=[N:35]2)[CH2:30][O:29]1.CCN(C(C)C)C(C)C>O1CCOCC1.C(OCC)(=O)C>[CH2:1]([C:8]1[CH:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[N:21]=[CH:22][N:23]=[C:24]([NH:39][C:37]4[CH:36]=[N:35][N:34]([CH2:33][CH:31]5[CH2:30][O:29][C:28]([CH3:40])([CH3:27])[O:32]5)[CH:38]=4)[N:25]=3)[CH2:16][CH2:15]2)=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 118023076HCID 118023076, compoundHCID 118023271HCID 118023271, compound

Product 1

HCID 118023134HCID 118023134, compoundYield 126.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-(4-(5-benzylpyrimidin-2-yl)piperazin-1-yl)-4-chloro-1,3,5-triazine (110 mg, 0.3 mmol), 1((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-4-amine (90 mg, 0.45 mmol) and Hunig's base (80 mg, 0.6 mmol) in 1,4-dioxane (4 mL) was stirred at 60° C. for 5 h. LCMS showed the reaction was completed. The reaction mixture was cooled to RT and diluted with ethyl acetate (40 mL). The organic phase was washed with water (40 mL) and brine (20 mL), dried over sodium sulfate, filtered and concentrated to give 4-(4-(5-benzylpyrimidin-2-yl)piperazin-1-yl)-N-(1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-4-yl)-1,3,5-triazin-2-amine (200 mg, crude) as a yellow solid, which was directly used in the next step without further purification. MS (ES+) C26H30N10O2 requires: 528, found: 529 [M+H]+.

Workup

  1. washThe organic phase was washed with water (40 mL) and brine (20 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-76d3e88f4e1b4b2b8d04d5829c1ca0f8
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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