Tetrahydrofuran → HCID 67250960, compound

HRID 335686Notes

Reaction equation

HRID 335686 reaction equation
[C:1]([NH:5][C:6]1[S:7][CH2:8][C:9]2([N:25]=1)[C:22]1[CH:21]=[C:20](Br)[CH:19]=[CH:18][C:17]=1[O:16][C:15]1[C:10]2=[CH:11][C:12]([Cl:24])=[CH:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].[N:26]1[CH:31]=[C:30](B(O)O)[CH:29]=[N:28][CH:27]=1.C1COCC1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([NH:5][C:6]1[S:7][CH2:8][C:9]2([N:25]=1)[C:10]1[CH:11]=[C:12]([Cl:24])[CH:13]=[CH:14][C:15]=1[O:16][C:17]1[C:22]2=[CH:21][C:20]([C:30]2[CH:31]=[N:26][CH:27]=[N:28][CH:29]=2)=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 67247268HCID 67247268, compound

Product 1

HCID 67250960HCID 67250960, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

A 10-20 mL microwave vial was charged with racemic-N-tert-butyl-2′-bromo-7′-chloro-spiro[1,3-thiazole-4,9′-xanthen]-2-amine (363 mg, 829 μmol), pyrimidin-5-ylboronic acid (257 mg, 2073 μmol), tetrakis(triphenylphosphine)palladium(0) (95.8 mg, 82.9 μmol), THF (8292 μl, 829 μmol), and potassium carbonate (3455 μl of a 1.2 M aqueous solution, 4146 μmol). The vial was covered with a blanket of Ar (g), capped, and heated in a Biotage Initiator microwave reactor for 1 h at 100° C. The organic layer was separated, dried over sodium sulfate, filtered, and evaporated. The residue was purified by chromatography on an 80-g Redi-Sep column, eluting with 0-50% EtOAc/Hexane to give rac-N-tert-butyl-2′-chloro-7′-(5-pyrimidinyl)spiro[1,3-thiazole-4,9′-xanthen]-2-amine as an orange-yellow solid. MS m/z=437.2 [M+H]+. Calc'd for C23H22ClN4OSS: 437.1.

Workup

  1. customcapped
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on an 80-g Redi-Sep column
  7. washeluting with 0-50% EtOAc/Hexane

Sources & evidence

ORD record
ord-9fd56f47757c496a899a119cab5e0285
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

Loading…