Water → HCID 57990348, compound

HRID 2281508Notes

Reaction equation

HRID 2281508 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:10]([I:11])=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[N:7]=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1.CCN(C(C)C)C(C)C.O>O1CCOCC1.CCOC(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:31][C:28]2[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)[C:5]2[C:10]([I:11])=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7732P-AnisidineHCID 81531DiisopropylethylamineHCID 579902932,4-dichloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 57990348HCID 57990348, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2,4-dichloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (260 mg, 0.556 mmol), p-anisidine (75 mg, 0.610 mmol) and DIEA (0.300 mL, 1.72 mmol) in dioxane (5 mL) was stirred at 110° C. for 20 h. Water and EtOAc were added. The organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 2-chloro-5-iodo-N-(4-methoxyphenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (257 mg).

Workup

  1. customThe organic phase was separated
  2. washwashed with 1N HCl
  3. dry with materialwith 5% NaHCO3, dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fafd34be122d4b878fdb8f9dac90275e
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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