Hydrochloric Acid → HCID 20468543, compound

HRID 1903315Notes

Reaction equation

HRID 1903315 reaction equation
[NH2:1][C:2]1[N:3]([CH2:21][O:22][CH:23]([CH3:25])[CH3:24])[C:4](=[O:20])[C:5]2[C:10]([CH:11]=O)=[CH:9][N:8]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[N:7]=1.[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[BH4-].[Na+].Cl>CO>[NH2:1][C:2]1[N:3]([CH2:21][O:22][CH:23]([CH3:24])[CH3:25])[C:4](=[O:20])[C:5]2[C:10]([CH2:11][NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:9][N:8]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 4311764Sodium borohydrideHCID 13187680HCID 13187680, compound

Product 1

HCID 20468543HCID 20468543, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 10 ml of dry methanol is dissolved 340 mg of 2-amino-7-benzyl-3-isopropyloxymethylpyrrolo[2,3-d]pyrimidin-4-one-5-carbaldehyde and 93 mg of aniline and the mixture is allowed to stand under stirring at room temperature for 60 min. The mixture is then cooled to 0° C. and treated with 38 mg of sodium borohydride for 2 hrs. The excess reagent is decomposed with HCl, the solvent is distilled off under reduced pressure, and the residue is purified by silica gel column chromatography to give 285 mg of 2-amino-7-benzyl-5-phenylaminomethyl-3-isopropyloxymethylpyrrolo[2,3-d]pyrimidin-4-one. The whole amount of the above product is dissolved in 28.5 ml of liquid ammonia-dimethoxyethane (1:1) and an excess of sodium metal shavings are added until a permanent blue color is observed for more than 5 min. To this mixture is added ammonium chloride to terminate the reaction and the whole system is allowed to stand at room temperature until the liquid ammonia is removed. The dimethoxyethane is then distilled off under reduced pressure and the residue is purified by silica gel column chromatography to give 128 mg of 2-amino-5-phenylaminomethyl-3-isopropyloxymethylpyrrolo[2,3-d]pyrimidin-4-one. This product is further dissolved in 50 ml of 2 N--HCl and after nitrogen purging, hydrolyzed by heating at 70° C. for 5 hrs. The solvent is then evaporated to dryness under reduced pressure to give 120 mg of the desired compound.

Workup

  1. temperatureThe mixture is then cooled to 0° C.
  2. distillationthe solvent is distilled off under reduced pressure
  3. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b0053d76d89b42e0a41372d427bec10f
Source dataset
uspto-grants-1984_03
Patent number
US04435569

Reaction notes

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