HCID 57833471, compound → HCID 57833230, compound

HRID 729967Notes

Reaction equation

HRID 729967 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:23]=[CH:22][C:12]([CH2:13][C:14]3[CH:19]=[CH:18][N:17]=[C:16]([C:20]#[N:21])[CH:15]=3)=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=1>CO.Cl.[Pd]>[NH2:21][CH2:20][C:16]1[CH:15]=[C:14]([CH2:13][C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:6]3[CH:5]=[C:4]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:3]=[C:2]([NH2:1])[N:7]=3)=[CH:23][CH:22]=2)[CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 1

HCID 57833471HCID 57833471, compound

Product 1

HCID 57833230HCID 57833230, compoundYield 11%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent2×

Procedure

10% Degussa Pd on carbon (15 mg, 0.14 mmol) was flushed with nitrogen then diluted in methanol (1 mL). 4-[4-(2-amino-6-phenyl-pyrimidin-4-ylamino)-benzyl]-pyridine-2-carbonitrile (Example 35, 90 mg, 0.24 mmol) in methanol (2 mL) and concentrated HCl (0.03 mL) were subsequently added, and the mixture was flushed again with nitrogen prior to placing a hydrogen balloon on the flask. The mixture was stirred at rt for 3 h then filtered through Celite® and concentrated. The residue was purified by prep HPLC to give N4-[4-(2-aminomethyl-pyridin-4-ylmethyl)-phenyl]-6-phenyl-pyrimidine-2,4-diamine (10 mg, 11%).

Workup

  1. customthe mixture was flushed again with nitrogen
  2. filtrationthen filtered through Celite®
  3. concentrationconcentrated
  4. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-f0b7c0e647a84eaea148ea29528e65df
Source dataset
uspto-grants-2009_09
Patent number
US07582646B2

Reaction notes

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