Ammonia → 5-((Benzyloxy)methyl)-2-butyl-7-iodo-5H-pyrrolo[3,2-d]pyrimidin-4-amine

HRID 1487245Notes

Reaction equation

[CH2:1]([O:8][CH2:9][N:10]1[C:18]2[C:17](Cl)=[N:16][C:15]([CH2:20][CH2:21][CH2:22][CH3:23])=[N:14][C:13]=2[C:12]([I:24])=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:25]>CC(O)C.CO.ClCCl>[CH2:1]([O:8][CH2:9][N:10]1[C:18]2[C:17]([NH2:25])=[N:16][C:15]([CH2:20][CH2:21][CH2:22][CH3:23])=[N:14][C:13]=2[C:12]([I:24])=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

5-((Benzyloxy)methyl)-2-butyl-4-chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine (1 g, 2.2 mmol) was suspended in 2-propanol (5 mL) and 35% (0.88) ammonia solution (4 mL). The reaction was stirred at 120° C. for 90 minutes in a Biotage Initiator microwave. A further 1 mL of 35% (0.88) ammonia solution was added to the reaction. The reaction was stirred at 120° C. for 90 minutes in a Biotage Initiator microwave. The reaction was evaporated in vacuo to yield a pale yellow oil. The oil was dissolved in the minimum volume of 20% methanol in dichloromethane and purified by chromatography on silica using a gradient of 0-100% ethyl acetate in cyclohexane gradient over 80 minutes. Fractions were combined and evaporated in vacuo to yield the title compound as a colourless oil (768 mg).

Workup

stirringThe reaction was stirred at 120° C. for 90 minutes in a Biotage Initiator microwave
customThe reaction was evaporated in vacuo
customto yield a pale yellow oil
custompurified by chromatography on silica using a gradient of 0-100% ethyl acetate in cyclohexane gradient over 80 minutes
customevaporated in vacuo

Sources & evidence

ORD record: ord-1bcb917d59d448a88c279385abc9c9fd
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428512B2

Reaction notes

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