Acetate → HCID 18954426, compound

HRID 1534394Notes

Reaction equation

HRID 1534394 reaction equation
[C:1]([O-:4])(=O)[CH3:2].O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].C(=O)=O.[NH2:19][C:20]1[N:25]=[C:24]([Cl:26])[CH:23]=[C:22](Cl)[N:21]=1.C([N:30](CC)CC)C.[OH-].[Na+].[CH2:37](O)[CH2:38][CH2:39][CH3:40]>O>[NH2:19][C:20]1[N:25]=[C:24]([Cl:26])[CH:23]=[C:22]([NH:30][C:2]2([CH2:1][OH:4])[CH2:40][CH2:39][CH:38]=[CH:37]2)[N:21]=1

Participants

9

Reactant 7

HCID 175AcetateHCID 2631-ButanolHCID 280Carbon DioxideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 655222-Amino-4,6-dichloropyrimidineHCID 17749109Barium hydroxide, octahydrate

Product 1

HCID 18954426HCID 18954426, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

cis-4-Acetamidocyclopent-2-enemethyl acetate [U.S. Pat. No. 4,268,672] (14.88 g, 0.073 mol) and barium hydroxide octahydrate (46.19 g, 0.146 mol) were refluxed in water (300 mL) under nitrogen for 18 hours. The resulting solution was neutralized with carbon dioxide. The precipitate was washed with water, then ethanol. The combined filtrate-wash was evaporated to a syrup (11.16 g) which was condensed with 2-amino-4,6-dichloropyrimidine (23.91 g, 0.146 mol) and triethylamine (30.5 mL, 0.219 mol) in refluxing 1-butanol (100 mL) for 1.5 hours. After addition of 1N NaOH (73 mL), the resulting mixture was evaporated to dryness and the residual solid slurried in CHCl3 (200 mL). Unreacted 2-amino-4,6-dichloropyrimidine was filtered off and washed with chloroform (100 mL). The chloroform filtrate-wash was concentrated and chromatographed on a silica gel column. Additional pyrimidine starting material was eluted with 2.5% methanol-chloroform. The title compound was eluted with 3.5% methanol-chloroform as an off-white solid foam (15.90 g, 91%).

Workup

  1. washThe precipitate was washed with water
  2. washThe combined filtrate-wash
  3. customwas evaporated to a syrup (11.16 g) which
  4. customthe resulting mixture was evaporated to dryness
  5. filtrationwas filtered off
  6. washwashed with chloroform (100 mL)
  7. washThe chloroform filtrate-wash
  8. concentrationwas concentrated
  9. customchromatographed on a silica gel column
  10. washAdditional pyrimidine starting material was eluted with 2.5% methanol-chloroform
  11. washThe title compound was eluted with 3.5% methanol-chloroform as an off-white solid foam (15.90 g, 91%)

Sources & evidence

ORD record
ord-2a9a001b26df4ad89d92a386ee6df9c8
Source dataset
uspto-grants-1992_02
Patent number
US05089500

Reaction notes

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