Cyclopropylamine → 2-chloro-N-cyclopropyl-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 2381593Notes

Reaction equation

HRID 2381593 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.[CH:23]1([NH2:26])[CH2:25][CH2:24]1.CCN(C(C)C)C(C)C>C(O)CCC>[Cl:1][C:2]1[N:3]=[C:4]([NH:26][CH:23]2[CH2:25][CH2:24]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

5

Reactant 3

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 579902932,4-dichloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 579903252-chloro-N-cyclopropyl-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 69.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a mixture of 2,4-dichloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (0.414 g, 0.88 mmol) in nBuOH (1.5 mL) was added cyclopropylamine (0.0674 mL, 1.06 mmol) and DIPEA (0.188 mL, 1.06 mmol). After stirring at ambient temperature for 15 h, the resulting precipitate was collected by filtration to give 2-chloro-N-cyclopropyl-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.3 g).

Workup

  1. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-73cfde777b52419fb16a9a4a49520ba9
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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