Water → HCID 19350008, compound

HRID 1637124Notes

Reaction equation

HRID 1637124 reaction equation
C[O-].[Na+].[CH:4]1([O:9][C:10]2[CH:11]=[C:12]([CH:18]([CH2:32][C:33]3[O:34][CH:35]=[C:36]([CH3:38])[N:37]=3)[C:19]#[C:20][C:21]3[CH:22]=[N:23][C:24]([NH:27]C(=O)CC)=[N:25][CH:26]=3)[CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[CH2:8][CH2:7][CH2:6][CH2:5]1.O>CO>[NH2:27][C:24]1[N:23]=[CH:22][C:21]([C:20]#[C:19][CH:18]([C:12]2[CH:13]=[CH:14][C:15]([O:16][CH3:17])=[C:10]([O:9][CH:4]3[CH2:8][CH2:7][CH2:6][CH2:5]3)[CH:11]=2)[CH2:32][C:33]2[O:34][CH:35]=[C:36]([CH3:38])[N:37]=2)=[CH:26][N:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 54131267HCID 54131267, compound

Product 1

HCID 19350008HCID 19350008, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of sodium methoxide (0.12 g, 2.2 mmol) in methanol (20 mL) was added (+/-)-3-(3-cyclopentyloxy-4-methoxyphenyl)4(4-methyloxazol-2-yl)-1-(2-propionamidopyrimidin-5-yl)but-1-yne (0.29 g, 0.60 mmol). The mixture was heated at reflux for 1 h (forming a solution) and was cooled. Water was added and the mixture was extracted three times with dichloromethane, was dried (magnesium sulfate) and the solvent was evaporated and gave the titled compound (64%) as an off-white solid, mp 103-105° C. Anal (C24H26N4O3 ·0.6 H2O) calcd: C, 67.15, H, 6.39, N, 13.05; C, 67.07, H, 6.22, N, 12.67.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h (
  3. customforming a solution) and
  4. temperaturewas cooled
  5. extractionthe mixture was extracted three times with dichloromethane
  6. dry with materialwas dried (magnesium sulfate)
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cb88fd6957c64e898bcb55dd2b7efdfc
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

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