Potassium Carbonate → tert-Butyl 4-fluoro-2-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)phenylcarbamate

HRID 1363169Notes

Reaction equation

HRID 1363169 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[N:13]=[C:12]([S:14][C:15]#[N:16])[C:11]([N+:17]([O-:19])=[O:18])=[CH:10][N:9]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[C:23]([N+:35]([O-])=O)[CH:22]=1>C(#N)C.[Cl-].[Na+].O>[F:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[C:23]([NH:35][C:8]2[N:13]=[C:12]([S:14][C:15]#[N:16])[C:11]([N+:17]([O-:19])=[O:18])=[CH:10][N:9]=2)[CH:22]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 210775882-Chloro-5-nitropyrimidin-4-yl thiocyanateHCID 59705030(4-Fluoro-2-nitro-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 59704889tert-Butyl 4-fluoro-2-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)phenylcarbamateYield 80.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Potassium carbonate (207 mg) was added to a stirred solution of 2-chloro-5-nitro-4-thiocyanatopyrimidine (108 mg) and tert-butyl 4-fluoro-2-nitrophenylcarbamate (113 mg) in ACN (5 mL) and stirred for 15 hr. The solution was diluted with brine and extracted with EtOAc (2×). The combined organics were evaporated and purified via column chromatography, elution with 30% EtOAc/Hex gave the titled compound (144 mg, 71% yield). 1H-NMR (300 MHz, DMSO-d6) δ 10.5 (br s, 1H), 9.3 (br s, 1H), 8.9 (br s, 1H), 7.7-7.4 (m, 2H), 7.1 (br s, 1H), 1.5 (s, 9H), 1.5 (s, 9H); MH+=407, 307 (-BOC), 351 (-tBu).

Workup

  1. extractionextracted with EtOAc (2×)
  2. customThe combined organics were evaporated
  3. custompurified via column chromatography, elution with 30% EtOAc/Hex

Sources & evidence

ORD record
ord-df620f76ea3c4f64909c5f0f0d131fa9
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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