Tin tetrachloride → HCID 118294255, compound

HRID 2205181Notes

Reaction equation

[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][NH:5][C:4](=[O:9])[N:3]=1.C(O[CH:14]1[C@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@:16]([CH2:34][O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([CH:31]([F:33])[F:32])[O:15]1)(=O)C.Cl[Sn](Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>CC#N>[C:20]([O:19][C@@H:18]1[C@H:17]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@:16]([CH2:34][O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)([CH:31]([F:32])[F:33])[O:15][C@H:14]1[N:5]1[CH:6]=[C:7]([Cl:8])[C:2]([NH2:1])=[N:3][C:4]1=[O:9])(=[O:22])[CH3:21]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 4-amino-5-chloropyrimidin-2(1H)-one 28 (0.336 g, 2.33 mmol) in anhydrous CH3CN (10 mL) was added BSA (0.945 g, 4.64 mmol) portion-wise while maintaining the reaction temperature at 25° C. After the reaction mixture became clear, compound 5 (0.54 g, 1.16 mmol) in CH3CN (2 mL) and SnCl4 (1.2 g, 4.64 mmol) was added into the mixture. The mixture was stirred at 65° C. for 1 h, then cooled and poured into saturated NaHCO3 solution (20 mL). The organic phase was extracted with ethyl acetate, washed with water, brine, dried (Na2SO4) and evaporated to dryness under reduced pressure. Purification by flash silica gel chromatography [dichloromethane:methanol (40:1)] gave 29 as a white solid (0.24 g, 31%). LC-MS: (M+H)+=550.1

Workup

temperaturecooled
extractionThe organic phase was extracted with ethyl acetate
washwashed with water, brine
dry with materialdried (Na2SO4)
customevaporated to dryness under reduced pressure
customPurification by flash silica gel chromatography [dichloromethane:methanol (40:1)]

Sources & evidence

ORD record: ord-51ae9e32612e44d198053b5bbe07ebe2
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09370569B2

Reaction notes

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