Methylamine → 3-({5-cyano-6-[(2,2-dimethylpropyl)(methyl)amino]-2-(methylamino)pyrimidin-4-yl}amino)-N-methoxy-4-methylbenzamide

HRID 1666077Notes

Reaction equation

HRID 1666077 reaction equation
[C:1]([C:3]1[C:4]([NH:19][C:20]2[CH:21]=[C:22]([CH:28]=[CH:29][C:30]=2[CH3:31])[C:23]([NH:25][O:26][CH3:27])=[O:24])=[N:5][C:6](S(C)=O)=[N:7][C:8]=1[N:9]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:10])#[N:2].[CH3:32][NH2:33]>>[C:1]([C:3]1[C:4]([NH:19][C:20]2[CH:21]=[C:22]([CH:28]=[CH:29][C:30]=2[CH3:31])[C:23]([NH:25][O:26][CH3:27])=[O:24])=[N:5][C:6]([NH:33][CH3:32])=[N:7][C:8]=1[N:9]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:10])#[N:2]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 589285033-{5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-methanesulfinyl-pyrimidin-4-ylamino}-N-methoxy-4-methyl-benzamide

Product 1

HCID 98229063-({5-cyano-6-[(2,2-dimethylpropyl)(methyl)amino]-2-(methylamino)pyrimidin-4-yl}amino)-N-methoxy-4-methylbenzamide

Procedure

3-{5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-methanesulfinyl-pyrimidin-4-ylamino}-N-methoxy-4-methyl-benzamide (33 mg) and methylamine (2.5 mL, 2 M in THF) were heated in a sealed tube at 75° C. for overnight. After the solvent was removed in vacuo, the residue was purified by silica gel column chromatography to afford the product (7.3 mg). MS (m/z): 412 (M+H).

Workup

  1. customAfter the solvent was removed in vacuo
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ab50513e136b484f9e57a26764f4817d
Source dataset
uspto-grants-2011_10
Patent number
US08044040B2

Reaction notes

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