Potassium Phosphate, Tribasic → HCID 57556450, compound

HRID 556378Notes

Reaction equation

HRID 556378 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][O:9][C:10](=[O:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:3]=1.[CH2:17]([O:19][C:20]([C:22]1[C:23]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][C:24]=2[S:25][CH:26]=1)=[O:21])[CH3:18].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN1C(=O)CCC1.O>[CH2:17]([O:19][C:20]([C:22]1[C:23]2[CH:30]=[CH:29][C:28]([O:31][C:2]3[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][O:9][C:10](=[O:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:3]=3)=[CH:27][C:24]=2[S:25][CH:26]=1)=[O:21])[CH3:18]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66992863HCID 66992863, compoundHCID 86626631HCID 86626631, compound

Product 1

HCID 57556450HCID 57556450, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 324 mg (1.33 mMol) hexanoic acid 4-chloro-pyrimidin-2-ylmethyl ester, 313 mg (1.41 mMol) 6-hydroxy-benzo[b]thiophene-3-carboxylic acid ethyl ester (Step 12.3) and 312 mg (1.47 mMol) K3PO4 in 5 ml NMP is stirred for 45 h at 60° C. The reaction mixture is dissolved in water and EtOAc, the aq. phase separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; CH2Cl2/ether 59:1→9:1) and crystallization from hexane gives the title compound: m.p.: 51° C.; MS: [M+1]+=429; TLC(CH2Cl2/ether 19:1): Rf=0.28.

Workup

  1. customEtOAc, the aq. phase separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customChromatography (Combi Flash; CH2Cl2/ether 59:1→9:1) and crystallization from hexane

Sources & evidence

ORD record
ord-db6c43a61852484eac058230971f4581
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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