HCID 58504435, compound → HCID 58504523, compound

HRID 2367323Notes

Reaction equation

HRID 2367323 reaction equation
[N:1]([CH2:4][C@H:5]1[O:10][CH2:9][C@@H:8]([CH3:11])[N:7]([C:12]2[CH:17]=[C:16]([Cl:18])[N:15]=[C:14]([NH2:19])[N:13]=2)[CH2:6]1)=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][CH2:4][C@H:5]1[O:10][CH2:9][C@@H:8]([CH3:11])[N:7]([C:12]2[CH:17]=[C:16]([Cl:18])[N:15]=[C:14]([NH2:19])[N:13]=2)[CH2:6]1

Participants

4

Reactant 1

HCID 58504435HCID 58504435, compound

Product 1

HCID 58504523HCID 58504523, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 4-[(2S,5R)-2-(azidomethyl)-5-methyl-4-morpholinyl]-6-chloro-2-pyrimidinamine (890 mg, 3.14 mmol) and 10% Pd/C (95 mg, 0.09 mmol) in ethanol (35 mL) was stirred under an atmosphere of hydrogen for 1.5 hours, then filtered through a pad of celite. The filtrate was concentrated in vacuo to give the title compound (778 mg, about 85% purity) as a white solid. LC-MS (ES) m/z=258, 260 [M+H]+.

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-23f4b89e64da4e0282c1778f9fc7c4d4
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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