Acetic Acid → HCID 58095180, compound

HRID 2282330Notes

Reaction equation

HRID 2282330 reaction equation
C([N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[C:9]1[S:13][C:12]([C:14]2[C:15]3[N:22]=[C:21]([NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])[S:20][C:16]=3[N:17]=[CH:18][N:19]=2)=[CH:11][C:10]=1[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[Cl:35])C=C.C(O)(=O)C.C1([SiH3])C=CC=CC=1.O>C(Cl)Cl.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:24]([NH:23][C:21]1[S:20][C:16]2[N:17]=[CH:18][N:19]=[C:14]([C:12]3[S:13][C:9]([C:5]4[NH:6][CH:7]=[CH:8][N:4]=4)=[C:10]([C:28]4[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=4[Cl:35])[CH:11]=3)[C:15]=2[N:22]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 12752PhenylsilaneHCID 58095024HCID 58095024, compound

Product 1

HCID 58095180HCID 58095180, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of 7-[5-(1-allyl-1H-imidazol-2-yl)-4-(2,4-dichlorophenyl)-2-thienyl]-N-(tert-butyl)[1,3]thiazolo[5,4-d]pyrimidin-2-amine (100 mg, 0.185 mmol) and acetic acid (2 mL, 40 mmol) in DCM (6 mL) was degassed with vacuum and then the atmosphere was replaced with nitrogen. To the mixture, tetrakis(triphenylphosphine)palladium(0) (10.7 mg, 0.00923 mmol) and phenylsilane (0.136 mL, 1.11 mmol) were added. The resulting mixture was stirred at 40° C. for 30 min. The solution was allowed to cool to rt, followed by adding water and DCM. After being stirred for 10 min, the organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Column chromatography was performed to yield the title compound (46.0 mg, 50%) as a pale yellow solid. LCMS: (AA) ES+ 501, 503. 1H NMR (400 MHz, d6-DMSO) δ: 11.84 (bs, 1H), 8.69 (bs, 1H), 8.63 (s, 1H), 8.43 (s, 1H), 7.73 (d, J=2.0 Hz, 1H), 7.46-7.43 (m, 1H), 7.34 (d, J=8.3 Hz, 1H), 7.14 (bs, 1H), 6.98 (bs, 1H), 1.47 (s, 9H).

Workup

  1. temperatureto cool to rt
  2. stirringAfter being stirred for 10 min
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-934460f8d1f845d28470db5804be2eec
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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