Water → HCID 178427345, compound

HRID 645677Notes

Reaction equation

HRID 645677 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1.[NH2:22][C:23]1[CH:31]=[C:30]2[C:26]([C:27]([CH3:32])=[N:28][NH:29]2)=[CH:25][CH:24]=1.C(N(CC)CC)C.O>C(O)CCC.CCOC(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:22][C:23]2[CH:31]=[C:30]3[C:26]([C:27]([CH3:32])=[N:28][NH:29]3)=[CH:25][CH:24]=2)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 534868282,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidineHCID 178434350HCID 178434350, compound

Product 1

HCID 178427345HCID 178427345, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (200 mg, 0.585 mmol), 6-amino-3-methylindazole (94 mg, 0.64 mmol) and triethylamine (TEA) (0.200 mL, 1.44 mmol) in n-butyl alcohol (n-BuOH) (5 mL) was heated at 110° C. overnight. After cooling down, H2O and EtOAc were added. The organic phase was separated, washed with 1N HCl, followed by 5% NaHCO3, before being dried over Na2SO4 and concentrated in vacuo to give 2-chloro-N-(3-methyl-1H-indazol-6-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (260 mg).

Workup

  1. temperatureAfter cooling down
  2. customThe organic phase was separated
  3. washwashed with 1N HCl
  4. dry with materialbefore being dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a2218b1a0474e85bd600032a0c2b502
Source dataset
uspto-grants-2010_04
Patent number
US07705004B2

Reaction notes

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