Borane → HCID 44555151, compound

HRID 2207565Notes

Reaction equation

HRID 2207565 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][CH:6]=1.[Li]CCCC.B.Cl[C:14]1[C:15]2[N:23]=[N:22][N:21]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][O:32][CH3:33])[N:26]=3)[C:16]=2[N:17]=[C:18]([NH2:20])[N:19]=1>C1COCC1.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>[CH3:33][O:32][CH2:31][C:27]1[N:26]=[C:25]([CH2:24][N:21]2[C:16]3[N:17]=[C:18]([NH2:20])[N:19]=[C:14]([C:4]4[S:5][CH:6]=[C:2]([CH3:1])[N:3]=4)[C:15]=3[N:23]=[N:22]2)[CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 6331BoraneHCID 127484-MethylthiazoleHCID 86655326HCID 86655326, compoundHCID 178418339Butyllithium

Product 1

HCID 44555151HCID 44555151, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-methylthiazole (0.15 mL, 1.65 mmol) in dry THF (7.5 mL) was cooled to −78° C. under nitrogen, treated with n-BuLi (1.0 mL, 1.65 mmol) and stirred for 30 minutes, then ZnCl (1-M, 1.65 mL, 1.65 mmol) was added, and the reaction mixture was warmed to room temperature. 7-Chloro-3-(6-methoxymethylpyridin-2-ylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-amine (250 mg, 0.825 mmol) was then added followed by Pd(PPh3)4 (48 mg, 0.04 mmol) and the reaction mixture heated to reflux for 1 h. The reaction mixture was cooled to room temperature, quenched with ammonium chloride and extracted with ethyl acetate. The organic phase was washed with water, dried and concentrated in vacuo. The crude product was purified by chromatography (eluant:EtOAc-heptane 1:1 to 2:1) to give the title compound (38 mg, 13%) as a yellow solid.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 1 h
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customquenched with ammonium chloride
  5. extractionextracted with ethyl acetate
  6. washThe organic phase was washed with water
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by chromatography (eluant:EtOAc-heptane 1:1 to 2:1)

Sources & evidence

ORD record
ord-81ac0f45f25f4d1baec0abf1e92621b4
Source dataset
uspto-grants-2016_06
Patent number
US09376443B2

Reaction notes

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