Water → HCID 58280073, compound

HRID 2189120Notes

Reaction equation

HRID 2189120 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([O:14][C:15](=[O:24])[CH2:16][O:17][C@H:18]1[CH2:22][CH2:21][C@H:20]([NH2:23])[CH2:19]1)([CH3:13])([CH3:12])[CH3:11].Cl[C:26]1[C:27]2[C:34]([C:35]3[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=3)=[C:33]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[O:32][C:28]=2[N:29]=[CH:30][N:31]=1.O>CN(C=O)C>[C:10]([O:14][C:15](=[O:24])[CH2:16][O:17][C@H:18]1[CH2:22][CH2:21][C@@H:20]([NH:23][C:26]2[C:27]3[C:34]([C:35]4[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=4)=[C:33]([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)[O:32][C:28]=3[N:29]=[CH:30][N:31]=2)[CH2:19]1)([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidineHCID 131730082HCID 131730082, compound

Product 1

HCID 58280073HCID 58280073, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Add 0.86 ml (5 2 mmol) of diisopropylethylamine to a mixture of 560.4 mg of (+/−)-cis/trans-[(3-aminocyclopentyl)oxy]acetic acid tert-butyl ester (crude product, approx. 2.60 mmol) and 964.3 mg (2.86 mmol) of 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine in 2.0 ml of DMF. Heat the reaction mixture to 100° C. for 6 h. After cooling, add water and extract with dichloromethane. Wash the organic phase with satd. sodium hydrogencarbonate solution and satd. sodium chloride solution, dry over sodium sulphate and concentrate under reduced pressure. After drying under high vacuum, purify the product mixture by preparative RP-HPLC (eluent: acetonitrile/water gradient) and separate it into the cis/trans isomers.

Workup

  1. temperatureAfter cooling
  2. extractionextract with dichloromethane
  3. washWash the organic phase with satd
  4. dry with materialsodium chloride solution, dry over sodium sulphate
  5. concentrationconcentrate under reduced pressure
  6. customAfter drying under high vacuum
  7. custompurify the product mixture by preparative RP-HPLC (eluent: acetonitrile/water gradient)
  8. customseparate it into the cis/trans isomers

Sources & evidence

ORD record
ord-4f96d135d79a40f2ae1982a94643c300
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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