Potassium Carbonate → Methyl 3-((6-amino-2-chloro-9H-purin-9-yl)methyl)benzoate

HRID 2197447Notes

Reaction equation

[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH2:11])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23]([O:25][CH3:26])=[O:24]>CN(C=O)C>[NH2:11][C:4]1[N:3]=[C:2]([Cl:1])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[CH2:19][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23]([O:25][CH3:26])=[O:24]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-chloro-6-aminopurine (1) (10 g, 58.97 mmol) and potassium carbonate (10 g, 744 mmol) in DMF (100 mL) was added methyl 3-(bromomethyl)benzoate (13.5 g, 58.93 mmol). The reaction mixture was heated to 60° C. for 90 minutes at which time the reaction was quenched by adding water. The quenched reaction mixture was extracted with ethyl acetate (3×50 mL) giving 16 g (86%) of Compound (2) as a white solid, which was used in the next step without further purification. 1H NMR (300 MHz, DMSO) δ 3.83 (s, 3H), 5.42 (s, 2H), 7.53 (m, 2H), 7.89 (m, 2H), 8.29 (s, 1H). LCMS: m/z for C14H12ClN5O2++H observed 318.1 at 1.99 minutes of a 3.5 minute run, gradient 5-95% CH3CN in H2O (C18 column).

Workup

customwas quenched
additionby adding water
customThe quenched reaction mixture
extractionwas extracted with ethyl acetate (3×50 mL)

Sources & evidence

ORD record: ord-f9fde1b834c04aaf9bc7f86259a59e8a
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338593B2

Reaction notes

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