HCID 58280086, compound → HCID 86653751, compound

HRID 2189039Notes

Reaction equation

HRID 2189039 reaction equation
[C:1]([O:5][C:6](=[O:16])[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([OH:15])[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:18]1[C:19]2[C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:25][O:24][C:20]=2[N:21]=[CH:22][N:23]=1>C1COCC1>[C:1]([O:5][C:6](=[O:16])[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([O:15][C:18]2[C:19]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:25][O:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 58280086HCID 58280086, compoundHCID 594278334-Chloro-5-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 86653751HCID 86653751, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolve 500 mg (2.17 mmol) of (+/−)-cis-{[3-hydroxycyclohexyl]oxy}acetic acid tert-butyl ester in 2.0 ml of dry THF, cool to 0° C. and add 1.24 ml (approx. 2.5 mmol) of a 2N solution of phosphazene base P2-t-Bu in THF. After removing the cooling, stir the mixture at RT for a further 30 min, before adding 500.7 mg (2.17 mmol) of 4-chloro-5-phenylfuro[2,3-d]pyrimidine at RT. Stir the mixture at RT overnight and then concentrate under reduced pressure. Purify the residue by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 10:1→8:1). The target product is obtained after further purification by means of RP-HPLC (eluent: acetonitrile/water). 380 mg (41.2% of theory) are isolated.

Workup

  1. customAfter removing the cooling
  2. stirringStir the mixture at RT overnight
  3. concentrationconcentrate under reduced pressure
  4. customPurify the residue by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 10:1→8:1)
  5. customThe target product is obtained
  6. customafter further purification by means of RP-HPLC (eluent: acetonitrile/water)
  7. custom380 mg (41.2% of theory) are isolated

Sources & evidence

ORD record
ord-814171ab3ae8402d8688880dd8ccc2a2
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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