Ethyl Acetate → HCID 57829801, compound

HRID 1855447Notes

Reaction equation

HRID 1855447 reaction equation
C(OC(=O)[CH2:10][N:11]([C:13]1[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]3)=[C:23]([O:33][CH3:34])[CH:22]=2)[N:14]=1)[CH3:12])C1C=CC=CC=1.[CH3:36][Mg]Cl.C([O:42][CH2:43][CH3:44])(=O)C>O1CCCC1>[CH3:34][O:33][C:23]1[CH:22]=[C:21]([NH:20][C:15]2[N:14]=[C:13]([N:11]([CH3:12])[CH2:10][C:43]([CH3:44])([OH:42])[CH3:36])[CH:18]=[C:17]([CH3:19])[N:16]=2)[CH:26]=[CH:25][C:24]=1[N:27]1[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 68913128HCID 68913128, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 57829801HCID 57829801, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ({2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-6-methyl-pyrimidin-4-yl}-methyl-amino)-acetic acid benzyl ester (32 mg, 0.07 mmol) in 2 mL of tetrahydrofurane was cooled in an ice-bath and treated with a 3 molar solution of methyl magnesium chloride in tetrahydrofurane (0.15 mL, 1.5 mmol). The mixture was stirred for 10 minutes in the ice-bath and for additional 2 hours at 20° C. Hydrolysis and extraction with ethyl acetate gave the title compound as a yellowish sticky gum (27 mg, 100%). MS ISP (m/e): 397.3 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.62 (s, 1H), 7.52 (s, 1H), 7.37 (d, 1H), 7.30-7.10 (m, 2H), 6.86 (s, 1H), 5.98 (s, 1H), 3.834 (s, 3H), 3.62 (s, 2H), 3.19 (s, 3H), 2.33 (s, 3H), 2.29 (s, 3H), 1.25 (s, 6H).

Sources & evidence

ORD record
ord-9c112113a939439997b8f272871256c2
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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