Water → HCID 58280123, compound

HRID 2189079Notes

Reaction equation

HRID 2189079 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[OH:25][C@@H:26]1[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@H:28]([CH2:39][CH2:40][C:41]([O:43][CH3:44])=[O:42])[CH2:27]1.O>CN(C=O)C>[CH3:44][O:43][C:41](=[O:42])[CH2:40][CH2:39][C@@H:28]1[CH2:27][C@H:26]([O:25][C:2]2[C:3]3[C:10]([C:11]4[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=4)=[C:9]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[O:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:31][CH2:30][N:29]1[C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33]

Participants

5

Reactant 3

HCID 962WaterHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidineHCID 58280132HCID 58280132, compound

Product 1

HCID 58280123HCID 58280123, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

Dissolve 631.7 mg (1.87 mmol) of 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine and 490 mg (1.71 mmol) of tert-butyl(2R,4R)-4-hydroxy-2-(3-methoxy-3-oxopropyl)piperidine-1-carboxylate in 1 ml of DMF, cool to −10° C. and add 1.02 ml (2.05 mmol) of phosphazene base P2-t-Bu (approx. 2 M solution in THF). Stir the reaction mixture at 0° C. for 1 h and then add to water. Extract three times with dichloromethane, combine the organic phases, wash with satd. sodium chloride solution and dry over magnesium sulphate. After concentrating under reduced pressure, purify the product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 20:1→3:1). 420 mg (38.1% of theory) of the target compound are obtained.

Workup

  1. extractionExtract three times with dichloromethane
  2. washwash with satd
  3. dry with materialsodium chloride solution and dry over magnesium sulphate
  4. concentrationAfter concentrating under reduced pressure
  5. custompurify the product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 20:1→3:1)
  6. custom420 mg (38.1% of theory) of the target compound are obtained

Sources & evidence

ORD record
ord-df47bbf72d594be8b86d5ccbe2c712a8
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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