Potassium Carbonate → HCID 22878251, compound

HRID 1489184Notes

Reaction equation

HRID 1489184 reaction equation
[NH2:1][C@H:2]1[C@@:7]([OH:9])([CH3:8])[C:6]([CH3:11])([CH3:10])[O:5][C:4]2[CH:12]=[CH:13][C:14]([C:16]3[N:20]([CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:19]=[N:18][N:17]=3)=[CH:15][C:3]1=2.Cl[C:30]1[CH:35]=[CH:34][N:33]=[C:32]([S:36][CH3:37])[N:31]=1.C(=O)([O-])[O-].[K+].[K+].CC(N(C)C)=O>O>[CH2:27]([O:26][C:24]([CH2:23][CH2:22][CH2:21][N:20]1[C:16]([C:14]2[CH:13]=[CH:12][C:4]3[O:5][C:6]([CH3:10])([CH3:11])[C@:7]([OH:9])([CH3:8])[C@H:2]([NH:1][C:30]4[CH:35]=[CH:34][N:33]=[C:32]([S:36][CH3:37])[N:31]=4)[C:3]=3[CH:15]=2)=[N:17][N:18]=[N:19]1)=[O:25])[CH3:28]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 971134-Chloro-2-methylthiopyrimidineHCID 57041522HCID 57041522, compound

Product 1

HCID 22878251HCID 22878251, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture containing (3S,4R)-4-amino-3,4-dihydro-6-(1-[3-ethoxycarbonylprop-1-yl]-1H-tetrazol-5-yl)-3-hydroxy-2,2,3-trimethyl-2H-benzo[b]pyran (see Preparation 55) (0.6 g), 4-chloro-2-methylthiopyrimidine (0.5 g), anhydrous potassium carbonate (0.7 g) and anhydrous dimethylacetamide (5 ml) was heated at 120° C. for 24 hours. On cooling to room temperature water (10 ml) was added and the mixture was extracted with ethyl acetate (2×50 ml). The extracts were combined and washed with water (50 ml) then concentrated in vacuo to give an oil which was purified by chromatography on silica eluting with dichloromethane containing ethyl acetate (40%). The product-containing fractions were combined and concentrated in vacuo to give a foam which was further purified by chromatography on silica eluting with dichloromethane containing isopropanol (3.3%). The product-containing fractions were combined and concentrated in vacuo to give an oil which was triturated with hexane to give the title compound as a foam, 0.077 g, m.p. 115°-130° C.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate (2×50 ml)
  3. washwashed with water (50 ml)
  4. concentrationthen concentrated in vacuo
  5. customto give an oil which
  6. customwas purified by chromatography on silica eluting with dichloromethane
  7. additioncontaining ethyl acetate (40%)
  8. concentrationconcentrated in vacuo
  9. customto give a foam which
  10. customwas further purified by chromatography on silica eluting with dichloromethane
  11. additioncontaining isopropanol (3.3%)
  12. concentrationconcentrated in vacuo
  13. customto give an oil which
  14. customwas triturated with hexane

Sources & evidence

ORD record
ord-890458a203324e46afe01481650c7a1d
Source dataset
uspto-grants-1997_10
Patent number
US05677324

Reaction notes

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