HCID 22640029, compound → HCID 22640042, compound

HRID 2415105Notes

Reaction equation

HRID 2415105 reaction equation
C([O:8][C:9]1[CH:25]=[CH:24][C:12]([CH2:13][NH:14][C:15]2[C:20](Cl)=[C:19]([CH3:22])[N:18]=[C:17]([CH3:23])[N:16]=2)=[CH:11][C:10]=1[O:26][CH2:27][CH:28]1[CH2:30][CH2:29]1)C1C=CC=CC=1.[H][H]>CO.C(O)(=O)C>[CH:28]1([CH2:27][O:26][C:10]2[CH:11]=[C:12]([CH2:13][NH:14][C:15]3[CH:20]=[C:19]([CH3:22])[N:18]=[C:17]([CH3:23])[N:16]=3)[CH:24]=[CH:25][C:9]=2[OH:8])[CH2:30][CH2:29]1

Participants

5

Reactant 2

HCID 22640029HCID 22640029, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 22640042HCID 22640042, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 2.0 g (4.7 mmol) of (4-benzyloxy-3-cyclopropylmethoxybenzyl)(5-chloro-2,6-dimethyl-pyrimidin-4-yl)amine (from example A5) in 50 ml of methanol and 20 ml of glacial acetic acid is admixed with 250 mg of Pd-on-carbon catalyst (type 38H, Johnson Matthey) and hydrogenated by circulation with hydrogen until about 2 equivalents of hydrogen (about 350 ml) have been taken up. After filtration to remove the catalyst, the solution is concentrated and the residue is chromatographed on silica gel (mobile phase: toluene/dioxane/ammonia=2:1:0.05). The fractions with Rf=0.15 are collected and concentrated. The residue (1.5 g), which is of poor solubility, is reacted further without additional purification (see example 7).

Workup

  1. filtrationAfter filtration
  2. customto remove the catalyst
  3. concentrationthe solution is concentrated
  4. customthe residue is chromatographed on silica gel (mobile phase: toluene/dioxane/ammonia=2:1:0.05)
  5. customThe fractions with Rf=0.15 are collected
  6. concentrationconcentrated
  7. customis reacted further without additional purification (see example 7)

Sources & evidence

ORD record
ord-7c845ae89dc044f8bbb79d17e6a17bc8
Source dataset
uspto-grants-2004_11
Patent number
US06818642B2

Reaction notes

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