Diisopropylethylamine → {2-[5-(4-Fluorophenylcarbamoyl)-2-methylsulfanylpyrimidin-4-ylamino]-ethyl}carbamic acid tert-butyl ester

HRID 348492Notes

Reaction equation

HRID 348492 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].CCN(C(C)C)C(C)C.[F:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([C:31]2[C:32](Cl)=[N:33][C:34]([S:37][CH3:38])=[N:35][CH:36]=2)=[O:30])=[CH:24][CH:23]=1>CN(C=O)C.C(OCC)(=O)C>[C:7]([O:6][C:5](=[O:11])[NH:4][CH2:3][CH2:2][NH:1][C:36]1[C:31]([C:29](=[O:30])[NH:28][C:25]2[CH:24]=[CH:23][C:22]([F:21])=[CH:27][CH:26]=2)=[CH:32][N:33]=[C:34]([S:37][CH3:38])[N:35]=1)([CH3:8])([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 188588054-Chloro-2-methylsulfanylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide

Product 1

HCID 69523125{2-[5-(4-Fluorophenylcarbamoyl)-2-methylsulfanylpyrimidin-4-ylamino]-ethyl}carbamic acid tert-butyl esterYield 80.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl N-(2-aminoethyl)carbamate (0.500 g, 3.12 mmol) and DIPEA (0.83 mL, 4.68 mmol, 1.5 eq) was added to a solution of 4-chloro-2-methylsulfanylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (0.929 g, 3.12 mmol) in DMF (5.0 ml) and stirred under N2 overnight. The reaction mixture was diluted with ethyl acetate (50 mL) and washed twice with water (50 mL). Upon precipitation of product out of the organic layer of the mixture, the white solid was filtered, and recrystallized from hot ethyl acetate to yield 1.06 g (80%) of the titled product as a white solid. 1H NMR: (d6-DMSO) δ 10.21 (s, 1H), 8.56 (s, 1H), 7.64 (m, 2H), 7.16 (m, 2H), 6.92 (t, 1H), 3.48 (m, 2H), 3.30 (s, 3H), 3.11 (m, 2H), 1.31 (s, 9H); HPLC: Rt=4.32 min; MS (ESI): m/z 419.97 (M−H)−.

Workup

  1. washwashed twice with water (50 mL)
  2. customUpon precipitation of product out of the organic layer of the mixture
  3. filtrationthe white solid was filtered
  4. customrecrystallized from hot ethyl acetate

Sources & evidence

ORD record
ord-767a83d9a2954c68a60df6736ed56be7
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

Loading…