Methanol → HCID 69369740, compound

HRID 431058Notes

Reaction equation

HRID 431058 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]1[N:13]=[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([Cl:24])[CH:17]=2)[C:11]([C:25](=[O:28])[CH:26]=[CH2:27])=[CH:10][N:9]=1.[CH3:29][OH:30]>S(=O)(=O)(O)O>[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]1[N:13]=[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([Cl:24])[CH:17]=2)[C:11]([C:25]([CH2:26][CH2:27][O:30][CH3:29])=[O:28])=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 69369766HCID 69369766, compound

Product 1

HCID 69369740HCID 69369740, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A mixture of (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-(acryloyl)pyrimidine (31 mg), methanol (1 ml) and conc. sulfuric acid (one drop) is heated under reflux for 2 days. After the reaction is complete, the solvent is evaporated under reduced pressure, and the residue is separated by silica gel thin layer chromatography (solvent; chloroform:methanol=30:1) to give (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[(2-methoxyethyl)carbonyl]pyrimidine (27 mg) as colorless oil, MS (m/z): 435 (MH+).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 days
  3. customthe solvent is evaporated under reduced pressure
  4. customthe residue is separated by silica gel thin layer chromatography (solvent; chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-276510cdc0d347a4bddf5377173f7cbc
Source dataset
uspto-grants-2003_12
Patent number
US06656935B2

Reaction notes

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