HCID 86755723, compound → HCID 23299674, compound

HRID 1952769Notes

Reaction equation

HRID 1952769 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:11]=[C:12]([O:38][CH3:39])[C:13]([O:36][CH3:37])=[C:14]([CH:16]=[CH:17][C:18]([N:20]3[CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22](C(C)(C)C(O)=O)[NH:21]3)=[O:19])[CH:15]=2)=[CH:4][N:3]=1.NC1N=C(N)C(CC2C=C(OC)C(OC)=C(C=CC(N3CC4C(=CC=CC=4)[CH:61]([C:69](C)([CH3:73])[C:70]([O-:72])=[O:71])N3)=O)C=2)=CN=1>CO.[OH-].[Na+]>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:11]=[C:12]([O:38][CH3:39])[C:13]([O:36][CH3:37])=[C:14](/[CH:16]=[CH:17]/[C:18]([N:20]3[N:21]=[CH:22][C:23]4[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:29]3[C:69]([CH3:73])([CH3:61])[C:70]([OH:72])=[O:71])=[O:19])[CH:15]=2)=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 86755723HCID 86755723, compoundHCID 86755724HCID 86755724, compound

Product 1

HCID 23299674HCID 23299674, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 887MethanolSolvent

Procedure

Preparation of (E)-(RS)-2-(2-{3-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenyl -acryloyl}-1,2-dihydro-phthalazin-1-yl)-2-methyl-propionic acid ##STR14## To the solution of 50 mg of methyl (E)-(RS)-2-(2-{3-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenyl -acryloyl}-1,2-dihydro-phthalazin-1-yl)-2-methyl-propionate (Example 1.12) in 5 ml of methanol are added 3 drops of 2N sodium hydroxide solution and the mixture is held at reflux for 45 min. Subsequently, the mixture is concentrated, the residue is treated with ice-water and neutralized with 2N hydrochloric acid. The insoluble material is recrystallized from methylene/methanol. 41 mg of (E)-(RS)-2-(2-{3-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenyl]-acryloyl}-1,2-dihydro-phthalazin-1-yl)-2-methyl-propionic acid are isolated as a colorless solid. M.p=245° C., dec.

Workup

  1. temperatureat reflux for 45 min
  2. concentrationSubsequently, the mixture is concentrated
  3. additionthe residue is treated with ice-water and neutralized with 2N hydrochloric acid
  4. customThe insoluble material is recrystallized from methylene/methanol

Sources & evidence

ORD record
ord-3c641784359441ceae498a298ffe5c38
Source dataset
uspto-grants-2000_09
Patent number
US06114330

Reaction notes

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