(S)-4-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine → (S)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-4-(5-(1-methylpiperidin-4-yl)pyrimidin-2-yl)morpholine

HRID 1478566Notes

Reaction equation

HRID 1478566 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[CH:9]=[N:10][C:11]([N:14]3[CH2:19][CH2:18][O:17][C@H:16]([CH2:20][N:21]4[C:25]5=[N:26][C:27]([C:30]6[CH:31]=[N:32][N:33]([CH3:35])[CH:34]=6)=[CH:28][N:29]=[C:24]5[N:23]=[N:22]4)[CH2:15]3)=[N:12][CH:13]=2)[CH2:4][CH2:3]1>CO.C(Cl)Cl.[Pt]=O>[CH3:35][N:33]1[CH:34]=[C:30]([C:27]2[N:26]=[C:25]3[N:21]([CH2:20][C@H:16]4[O:17][CH2:18][CH2:19][N:14]([C:11]5[N:12]=[CH:13][C:8]([CH:5]6[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]6)=[CH:9][N:10]=5)[CH2:15]4)[N:22]=[N:23][C:24]3=[N:29][CH:28]=2)[CH:31]=[N:32]1

Participants

5

Reactant 1

HCID 73504290(S)-4-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine

Product 1

HCID 118364858(S)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-4-(5-(1-methylpiperidin-4-yl)pyrimidin-2-yl)morpholineYield 18%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-4-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine 75 mg (0.16 mmol) was dissolved in methanol 3 ml and methylene chloride 2 ml, and an excess of platinum oxide was added. The mixture was degassed, and a hydrogen balloon was connected, followed by reaction at room temperature for 1 day. After the reaction, the platinum oxide was removed using a celite filter, and separated by PLC (methylene chloride:methanol=5:1) to give a yellow solid 13.3 mg (18%).

Workup

  1. customThe mixture was degassed
  2. customfollowed by reaction at room temperature for 1 day
  3. customAfter the reaction
  4. customthe platinum oxide was removed
  5. filtrationfilter
  6. customseparated by PLC (methylene chloride:methanol=5:1)

Sources & evidence

ORD record
ord-173bc51d6e884626b09e5f21ec4e9628
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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