HCID 22640029, compound → HCID 22640018, compound

HRID 2415104Notes

Reaction equation

HRID 2415104 reaction equation
C([O:8][C:9]1[CH:25]=[CH:24][C:12]([CH2:13][NH:14][C:15]2[C:20]([Cl:21])=[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>[Cl:21][C:20]1[C:15]([NH:14][CH2:13][C:12]2[CH:24]=[CH:25][C:9]([OH:8])=[C:10]([O:26][CH2:27][CH:28]3[CH2:30][CH2:29]3)[CH:11]=2)=[N:16][C:17]([CH3:23])=[N:18][C:19]=1[CH3:22]

Participants

5

Reactant 2

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

Product 1

HCID 22640018HCID 22640018, 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 1 equivalent of hydrogen (about 190 ml) has 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=0.35 are collected and concentrated. After crystallization from diisopropyl ether, 550 mg (35%) of the title compound are isolated as a beige powder. m.p.: 123-125° C.

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=0.35 are collected
  6. concentrationconcentrated
  7. customAfter crystallization from diisopropyl ether, 550 mg (35%) of the title compound
  8. customare isolated as a beige powder

Sources & evidence

ORD record
ord-b8b23efebb1f458aa026d3e06fe38446
Source dataset
uspto-grants-2004_11
Patent number
US06818642B2

Reaction notes

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