Formic Acid → HCID 135995010, compound

HRID 414993Notes

Reaction equation

N1C=CN=C1.C(N(CC)CC)C.[CH:13](O)=[O:14].C(Cl)(=O)C(Cl)=O.[O:22]=[C:23]1[NH:28][C:27]([CH2:29][C:30]2[CH:34]=[CH:33][S:32][CH:31]=2)=[N:26][C:25]([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[C:24]1[C:41]#[N:42]>ClCCl>[CH:13]([N:38]1[CH2:37][CH2:36][N:35]([C:25]2[N:26]=[C:27]([CH2:29][C:30]3[CH:34]=[CH:33][S:32][CH:31]=3)[NH:28][C:23](=[O:22])[C:24]=2[C:41]#[N:42])[CH2:40][CH2:39]1)=[O:14]

Participants

Conditions

Temperature: 0 °C

Procedure

11.3 mg (0.17 mmol) of imidazole are introduced together with 33.6 mg (0.33 mmol) of triethylamine and 7.64 mg (0.17 mmol) of formic acid into 5 ml of dichloromethane under an argon atmosphere and cooled to 0° C. Then a solution of 21.1 mg (0.17 mmol) of oxalyl chloride in dichloromethane is added dropwise, and the mixture is then stirred for 15 min. 50 mg (0.17 mmol) of 6-oxo-4-(piperazin-1-yl)-2-(3-thienylmethyl)-1,6-dihydropyrimidine-5-carbonitrile are added, and the mixture is stirred at RT overnight. It is then washed with 1 N potassium bisulphate solution, the dichloromethane phase is dried over sodium sulphate and concentrated, and the residue is flash-chromatographed on silica gel (mobile phase: dichloromethane/methanol 100:1, 80:1, 60:1). 16 mg (29% of theory) of the title compound are obtained.

Workup

stirringthe mixture is stirred at RT overnight
washIt is then washed with 1 N potassium bisulphate solution
dry with materialthe dichloromethane phase is dried over sodium sulphate
concentrationconcentrated
customthe residue is flash-chromatographed on silica gel (mobile phase: dichloromethane/methanol 100:1, 80:1, 60:1)

Sources & evidence

ORD record: ord-40bc2a14dad545c1856b03bd8fad5dc6
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088769B2

Reaction notes

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