Morpholine → (5-(5-chloro-4-(methylamino)pyrimidin-2-ylamino)-1-methyl-1H-pyrazol-3-yl)(morpholino)methanone

HRID 2409102Notes

Reaction equation

HRID 2409102 reaction equation
[Cl:1][C:2]1[C:3]([NH:18][CH3:19])=[N:4][C:5]([NH:8][C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15]([OH:17])=O)[CH:10]=2)=[N:6][CH:7]=1.CN(C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH:53]1[CH2:58][CH2:57][O:56][CH2:55][CH2:54]1>CN(C)C=O>[Cl:1][C:2]1[C:3]([NH:18][CH3:19])=[N:4][C:5]([NH:8][C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15]([N:53]3[CH2:58][CH2:57][O:56][CH2:55][CH2:54]3)=[O:17])[CH:10]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 690837945-((5-Chloro-4-(methylamino)pyrimidin-2-yl)amino)-1-methyl-1H-pyrazole-3-carboxylic acid

Product 1

HCID 69081536(5-(5-chloro-4-(methylamino)pyrimidin-2-ylamino)-1-methyl-1H-pyrazol-3-yl)(morpholino)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 100 mL round bottom flask equipped with a stir bar was added 0.116 g of 5-(5-chloro-4-(methylamino)pyrimidin-2-ylamino)-1-methyl-1H-pyrazole-3-carboxylic acid, 0.19 g of o-benzotriazol-1-yl-tetramethyluronium hexafluorophosphate, 0.14 mL of diisopropylethylamine and 2 mL of dimethylformamide. After pre-activating for 10 minutes, 0.05 mL of morpholine was added and the reaction stirred at room temperature for 2 hours. The reaction was concentrated and purified by preparative reverse phase HPLC to yield 53.2 mg of (5-(5-chloro-4-(methylamino)pyrimidin-2-ylamino)-1-methyl-1H-pyrazol-3-yl)(morpholino)methanone. LCMS (Method A): [MH+]=352.0 at 2.80 min. 1H-NMR (DMSO): δ 9.47 (s, 1H), 7.86 (s, 1H), 7.15 (s, 1H), 6.78 (s, 1H), 3.74 (s, 3H), 3.61 (m, 8H), 2.88 (d, 3H). K1=0.16.

Workup

  1. customTo a 100 mL round bottom flask equipped with a stir bar
  2. concentrationThe reaction was concentrated
  3. custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-4c172328dbaf4c859ff91c5260fb4629
Source dataset
uspto-grants-2014_08
Patent number
US08815882B2

Reaction notes

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