Tributyl(prop-1-yn-1-yl)stannane → 2-chloro-N-(pentan-3-yl)-5-(prop-1-ynyl)pyrimidin-4-amine

HRID 2189281Notes

Reaction equation

Br[C:2]1[C:3]([NH:9][CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH2:15]([Sn](CCCC)(CCCC)C#CC)[CH2:16][CH2:17]C>C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:8][C:5]1[N:4]=[C:3]([NH:9][CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:2]([C:15]#[C:16][CH3:17])=[CH:7][N:6]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a microwave vial is added a solution of (5-Bromo-2-chloro-pyrimidin-4-yl)-(1-ethyl-propyl)-amine (0.5 g, 1.80 mmol) in anhydrous toluene (10 ml), tributyl(1-propynyl)-tin (1.1 ml, 3.6 mmol) and 2 mol % of Pd(PPh3)4 (41.5 mg, 0.036 mmol). The reaction is heated at 120° C. for 1 hr by employing microwave. The reaction mixture is diluted with EtOAc, washed with sat. NaHCO3 aqueous solution and water, dried over Na2SO4, and concentrated in vacuo. Purification with column chromatography (SiO2, 1:5 EtOAC/Hexane) gives 0.32 g of the desired product.

Workup

washwashed with sat. NaHCO3 aqueous solution and water
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customPurification with column chromatography (SiO2, 1:5 EtOAC/Hexane)

Sources & evidence

ORD record: ord-173a1de2347a49c1a1efcdd8537bfcde
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324225B2

Reaction notes

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