[2-Chloro-5-(3,3-diethoxy-prop-1-ynyl)-pyrimidin-4-yl]-(1-ethyl-propyl)-amine → 2-Chloro-6-diethoxymethyl-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 2189312Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:5]([C:14]#[C:15][CH:16]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])=[CH:4][N:3]=1>C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:14]=[C:15]([CH:16]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])[N:8]([CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:6]=2[N:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of [2-chloro-5-(3,3-diethoxy-prop-1-ynyl)-pyrimidin-4-yl]-(1-ethyl-propyl)-amine (326 mg, 1 mmol) in THF (2 mL) is added IN TBAF in THF (5 mL, 5 mmol) at ambient temperature. The reaction mixture is heated at 70° C. for 2 h. After cooling down, the mixture is concentrated in vacuo and purified by BIOTAGE column (EtOAc/heptane 5:5 to 40:60) to give 307 mg of 2-chloro-6-diethoxymethyl-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine as a light yellow oil.

Workup

temperatureAfter cooling down
concentrationthe mixture is concentrated in vacuo
custompurified by BIOTAGE column (EtOAc/heptane 5:5 to 40:60)

Sources & evidence

ORD record: ord-139fa4a520f04d8aa923fdad5cb360a2
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324225B2

Reaction notes

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