Iodine → 4-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 1750317Notes

Reaction equation

[Cl:1][C:2]1[C:3]2C=CN[C:4]=2[N:5]=[CH:6][N:7]=1.[OH-].[K+].[I:13]I.CI.S([O-])([O-])(=O)=S.[Na+].[Na+].[CH3:24][N:25]([CH:27]=O)[CH3:26]>>[Cl:1][C:2]1[C:3]2[C:4]([I:13])=[CH:27][N:25]([CH3:26])[C:24]=2[N:5]=[CH:6][N:7]=1

Participants

Reactant 6

HCID 807Iodine

HCID 6228Dimethylformamide

HCID 6328Methyl iodide

HCID 14797Potassium Hydroxide

HCID 24477Sodium Thiosulfate

HCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 426094624-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

Procedure

To a stirred solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (2 g, 13.0 mmol) in anhydrous DMF (40 ml) was added potassium hydroxide (2.19 g, 39.1 mmol) followed by iodine (3.64 g, 14.3 mmol). The mixture was stirred for 1 h. Methyl iodide (0.814 ml, 13.0 mmol) was added and the mixture stirred for a further 1 h. The mixture was poured into 20% w/w sodium thiosulfate solution (400 ml). The formed solid was collected by filtration and dried under vacuum to afford the title compound which was used in the next step without further purification. LCMS RT=1.12 min, [M(35Cl)+H]+=294.0, [M(37Cl)+H]+=295.9.

Workup

stirringthe mixture stirred for a further 1 h
filtrationThe formed solid was collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-db4c0eb5a86e4a6e9338a08ff4cbf3f4
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156853B2

Reaction notes

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