Sodium Cyanide → HCID 21057870, compound

HRID 2216286Notes

Reaction equation

[C-]#N.[Na+].[N:4]12CCN(CC1)C[CH2:5]2.[CH3:12][O:13][C:14]1[CH:36]=[CH:35][C:17]([CH2:18][NH:19][C:20]([C:22]2[C:23]([NH:29][CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[N:24][C:25](Cl)=[N:26][CH:27]=2)=[O:21])=[CH:16][CH:15]=1>O.CS(C)=O>[CH3:12][O:13][C:14]1[CH:36]=[CH:35][C:17]([CH2:18][NH:19][C:20]([C:22]2[C:23]([NH:29][CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[N:24][C:25]([C:5]#[N:4])=[N:26][CH:27]=2)=[O:21])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of NaCN (95 mg, 1.9 mmol) in water (1 ml) and DMSO (10 ml) are added 1,4-diazabicyclo[2,2,2]octane (48 mg, 0.43 mmol) and 2-chloro-4-(2,2-dimethyl-propylamino)-pyrimidine-5-carboxylic acid 4-methoxy-benzylamide (470 mg, 1.3 mmol) in DMSO (2 ml) successively at ambient temperature. After being stirred for 2 hours at 50° C., the reaction mixture is poured into cold water and extracted with AcOEt. The combined extracts are washed with water, brine and dried over MgSO4. The concentrated residue is purified by silica gel column chromatography (eluent:n-hexane:AcOEt=2:1) give 2-cyano-4-(2,2-dimethyl-propylamino)-pyrimidine-5-carboxylic acid 4-methoxy-benzylamide. Rf=0.45 (n-hexane:AcOEt=2:1). 1H NMR (400 MHz, DMSO-d6) δ 1.00 (s, 9H), 3.37 (d, 2H), 3.81 (s, 3H), 4.53 (d, 2H), 6.36 (brs, 1H), 6.89 (d, 2H), 7.25 (d, 2H), 8.28 (s, 1H), 9.08 (brs, 1H).

Workup

extractionextracted with AcOEt
washThe combined extracts are washed with water, brine
dry with materialdried over MgSO4
customThe concentrated residue is purified by silica gel column chromatography (eluent:n-hexane:AcOEt=2:1)

Sources & evidence

ORD record: ord-4928d72f48b046dc8c52bf4c2849bf5b
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112589B2

Reaction notes

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