Water → HCID 59380066, compound

HRID 2353666Notes

Reaction equation

HRID 2353666 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[CH3:14])[CH:5]=[C:4]([CH2:15][S:16]([CH:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])[N:3]=1.O.[C:23]([O:27][C:28]([NH:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1)=[O:29])([CH3:26])([CH3:25])[CH3:24].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C(COC)OC.C(O)C>[CH:19]([S:16]([CH2:15][C:4]1[CH:5]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[CH3:14])[N:7]=[C:2]([C:34]2[CH:33]=[CH:32][C:31]([NH:30][C:28](=[O:29])[O:27][C:23]([CH3:25])([CH3:24])[CH3:26])=[CH:36][CH:35]=2)[N:3]=1)(=[O:18])=[O:17])([CH3:21])[CH3:20]

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 3613184(4-Boc-Aminophenyl)Boronic AcidHCID 59380206HCID 59380206, compound

Product 1

HCID 59380066HCID 59380066, compoundYield 108.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

(3S)-4-{2-Chloro-6-[(isopropylsulfonyl)methyl]pyrimidin-4-yl}-3-methylmorpholine (2.0 g, 5.99 mmol) was dissolved in a solution of 18% DMF in a mixture of 7:3:2 dimethoxyethane:water:ethanol (16 mL). {4-[(Tert-butoxycarbonyl)amino]phenyl}boronic acid (2.13 g, 8.99 mmol), 2M sodium carbonate solution (8 mL) and dichlorobis(triphenylphosphine) palladium catalyst (211 mg, 0.30 mmol) were then added and the reaction refluxed at 90° C. for 2 hours under a nitrogen atmosphere. The reaction was allowed to cool to room temp then partitioned between ethyl acetate (20 mL) and water (20 mL). The organics were dried over magnesium sulphate, filtered and concentrated in vacuo. The cream solid obtained was chromatographed on silica, eluting with 0-50% ethyl acetate in DCM, to give the desired material as a brown solid (3.2 g).

Workup

  1. temperatureto cool to room temp
  2. customthen partitioned between ethyl acetate (20 mL) and water (20 mL)
  3. dry with materialThe organics were dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe cream solid obtained
  7. customwas chromatographed on silica
  8. washeluting with 0-50% ethyl acetate in DCM

Sources & evidence

ORD record
ord-2f5574c66097473bba1edc0134ced963
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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