Diisopropylethylamine → (S)-tert-butyl 2-((4-(4-(4-(5-bromopyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-1H-pyrazol-1-yl)methyl)-morpholine-4-carboxylate

HRID 522633Notes

Reaction equation

HRID 522633 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH2:14][C@H:15]3[O:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]3)[CH:13]=2)[N:3]=1.C(N(C(C)C)CC)(C)C.[Br:37][C:38]1[CH:39]=[N:40][C:41]([N:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)=[N:42][CH:43]=1>O1CCOCC1>[Br:37][C:38]1[CH:39]=[N:40][C:41]([N:44]2[CH2:45][CH2:46][N:47]([C:2]3[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]4[CH:10]=[N:11][N:12]([CH2:14][C@H:15]5[O:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]5)[CH:13]=4)[N:3]=3)[CH2:48][CH2:49]2)=[N:42][CH:43]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27571751-(5-Bromopyrimidin-2-yl)piperazineHCID 118022859(S)-tert-butyl 2-((4-(4-chloro-1,3,5-triazin-2-ylamino)-1H-pyrazol-1-yl)methyl)-morpholine-4-carboxylate

Product 1

HCID 118023021(S)-tert-butyl 2-((4-(4-(4-(5-bromopyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-1H-pyrazol-1-yl)methyl)-morpholine-4-carboxylateYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-tert-butyl 2-((4-(4-chloro-1,3,5-triazin-2-ylamino)-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate (1.8 g, 4.5 mmol) in dioxane (50 mL) was added diisopropylethylamine (4 mL) and 5-bromo-2-(piperazin-1-yl)pyrimidine (1.3 g, 5.5 mmol). The reaction mixture was stirred at room temperature for 2 hours. The solvents were removed, and the residue was washed with methanol (10 mL) to afford (S)-tert-butyl 2-((4-(4-(4-(5-bromopyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-1H-pyrazol-1-yl)methyl)-morpholine-4-carboxylate as a white solid (2.4 g, 89%), which was directly used in the next step without further purification. MS (ES+) C24H32BrN11O3 requires: 601, 603, found: 602, 604 [M+H]+.

Workup

  1. customThe solvents were removed
  2. washthe residue was washed with methanol (10 mL)

Sources & evidence

ORD record
ord-429e271ee4104319b70326c127833fc1
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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