Water → HCID 57504302, compound

HRID 1097984Notes

Reaction equation

HRID 1097984 reaction equation
[H-].[Na+].[NH2:3][C:4]1[S:5][CH:6]=[C:7]([CH3:9])[N:8]=1.[CH2:10]([O:12][CH:13]([S:19][C:20]1[N:25]=[CH:24][N:23]=[C:22]2[N:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH3:36])[N:27]=[CH:28][C:21]=12)[C:14](OCC)=[O:15])[CH3:11].O>C1COCC1.C(Cl)Cl>[CH2:10]([O:12][CH:13]([S:19][C:20]1[N:25]=[CH:24][N:23]=[C:22]2[N:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH3:36])[N:27]=[CH:28][C:21]=12)[C:14]([NH:3][C:4]1[S:5][CH:6]=[C:7]([CH3:9])[N:8]=1)=[O:15])[CH3:11]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 741432-Amino-4-methylthiazoleHCID 57504477HCID 57504477, compound

Product 1

HCID 57504302HCID 57504302, compoundYield 1.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (95%, 3.7 mg, 0.15 mmol) was added to a stirred solution of 2-amino-4-methylthiazol (17.6 mg, 0.154 mmol) in anhydrous THF (4 mL). The reaction mixture was kept at ambient temperature for 5 minutes before ethyl ethoxy{[1-(2-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]thio}acetate (50 mg, 0.129 mmol) was added. The reaction mixture was stirred at ambient temperature for 1 h. Water and DCM were added and the two phases were separated. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with a gradient consisting of 40-100% EtOAc in heptane) to give the title compound as a colourless oil (1.1 mg), 1H NMR (300 MHz, CDCl3) δ 10.03 (br s, 1H), 8.74 (s, 1H), 8.26 (s, 1H), 7.47 (m, 2H), 7.12 (m, 2H), 6.91 (s, 1H), 6.58 (s, 1H), 4.02 (m, 1H), 3.81 (m, 4H), 2.38 (s, 3H), 1.34 (t, 3H), HRMS: calcd for (M+H+) C20H21N6O3S2: 457.1116. Found: 457.1116.

Workup

  1. additionwas added
  2. customthe two phases were separated
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified with column chromatography (silica gel
  6. washeluting with a gradient

Sources & evidence

ORD record
ord-06aa12638dac4caebae2a849f1266563
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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