Potassium Phosphate, Tribasic → HCID 66780017, compound

HRID 1958012Notes

Reaction equation

HRID 1958012 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:14]2[N:15]=[C:16]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[S:17][C:13]=2[C:12](=[O:24])[N:11]=[CH:10]1.[CH2:25](B(O)O)[CH3:26].P([O-])([O-])([O-])=O.[K+].[K+].[K+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:25]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:14]2[N:15]=[C:16]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[S:17][C:13]=2[C:12](=[O:24])[N:11]=[CH:10]1)[CH3:26]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 521157Ethylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 66780548HCID 66780548, compound

Product 1

HCID 66780017HCID 66780017, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-[(2-bromophenyl)methyl]-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (120 mg, 0.295 mmol), ethylboronic acid (32.7 mg, 0.442 mmol) and potassium phosphate (125 mg, 0.589 mmol) in Toluene (2 mL) was charged into a microwave tube under N2, followed by the addition of S-Phos (12.10 mg, 0.029 mmol), and Pd(OAc)2 (3.31 mg, 0.015 mmol). The mixture was irradiated with microwave at 150° C. for 15 min. The solvent was removed and the residue was partitioned between DCM and brine. The organic layer was concentrated and the residue was purified by reverse phase HPLC (5% org˜50% org) to give the product (60 mg, 58%). LCMS (ES) m/z 357.1 (M+H)+, 1H NMR (400 MHz, CDCl3-d1)) δppm 8.50 (br, s, 1H), 7.38 (m, 1H), 7.33 (m, 1H), 7.25 (m, 1H), 7.09 (m, 1H), 5.48 (s, 2H), 3.86 (m, 4H), 3.69 (m, 4H), 2.71 (q, 2H), 1.25 (t, 3H).

Workup

  1. additionwas charged into a microwave tube under N2
  2. customThe mixture was irradiated with microwave at 150° C. for 15 min
  3. customThe solvent was removed
  4. customthe residue was partitioned between DCM and brine
  5. concentrationThe organic layer was concentrated
  6. customthe residue was purified by reverse phase HPLC (5% org˜50% org)

Sources & evidence

ORD record
ord-c3381c38c256467d9c33d2a9abb43d92
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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