6-chloro-N4-methylpyrimidine-4,5-diamine → 6-Chloro-8-(1-ethyl-1H-pyrazol-4-yl)-9-methyl-9H-purine

HRID 528036Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH3:9])[C:3]=1[NH2:10].[CH2:11]([N:13]1[CH:17]=[C:16]([CH:18]=O)[CH:15]=[N:14]1)[CH3:12]>CN(C=O)C.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[C:3]=1[N:10]=[C:18]([C:16]1[CH:15]=[N:14][N:13]([CH2:11][CH3:12])[CH:17]=1)[N:8]2[CH3:9]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 6-chloro-N4-methylpyrimidine-4,5-diamine (300 mg, 1.9 mmol) in anhydrous DMF (8 mL) were added 1-ethyl-1H-pyrazole-4-carbaldehyde (236 mg, 1.9 mmol) and Iron (III) chloride hexahydrate (0.51 g, 1.9 mmol). The dark brown solution was heated to 90° C. for 14 hour in an open air vessel. The reaction mixture was cooled to room temperature and poured over ice (20 g). The resulting precipitate was collected by vacuum filtration, and triturated with 10 mL of ethanol at 50° C. for 30 min. The solids were collected by vacuum filtration to give 514 mg of the title compound. 1H NMR (400 MHz, DMSO-d6): δ 8.66 (t, 2H), 8.19 (s, 1H), 4.25 (q, 2H), 3.95 (s, 3H), 1.43 (t, 3H); MS (EI) for C11H11ClN6: 263.3 (MH+).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationThe resulting precipitate was collected by vacuum filtration
customtriturated with 10 mL of ethanol at 50° C. for 30 min
filtrationThe solids were collected by vacuum filtration

Sources & evidence

ORD record: ord-9c63682f68d14f359ca1087139334be9
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346807B2

Reaction notes

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