Water → 2-[[3-(ureido)propyl][2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]-N-[2-(4-methoxyphenyl)ethyl]acetamide

HRID 2180061Notes

Reaction equation

HRID 2180061 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([C:20]1[CH:25]=[C:24]([CH3:26])[N:23]=[C:22]([N:27]2[CH:31]=[CH:30][N:29]=[CH:28]2)[N:21]=1)[CH2:6][C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:8].O.[O-:33][C:34]#[N:35].[K+]>N1C=CC=CC=1>[NH:1]([CH2:2][CH2:3][CH2:4][N:5]([C:20]1[CH:25]=[C:24]([CH3:26])[N:23]=[C:22]([N:27]2[CH:31]=[CH:30][N:29]=[CH:28]2)[N:21]=1)[CH2:6][C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:8])[C:34]([NH2:35])=[O:33]

Participants

5

Reactant 3

HCID 962Water2×HCID 98885472-[(3-aminopropyl)[2-(1H-imidazol-1-yl)6-methyl-4-pyrimidinyl]amino]-N-[2-(4-methoxyphenyl)ethyl]acetamideHCID 11378442Potassium cyanate

Product 1

HCID 99342442-[[3-(ureido)propyl][2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]-N-[2-(4-methoxyphenyl)ethyl]acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

To 2-[(3-aminopropyl)[2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]-N-[2-(4-methoxyphenyl)ethyl]acetamide (135 mg, 0.32 mmol) (a compound of formula (Yc6)) in pyridine (1.5 mL) was added water (1.5 mL) solution of potassium cyanate (64 mg, 0.76 mmol). The mixture was stirred and heated in an oil bath at 80° C. overnight. The mixture was poured into water and extracted with ethyl acetate (3×20 mL). The combined ethyl acetate fractions were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (9:1 CH3CN/NH4OH) to afford 2-[[3-(ureido)propyl][2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]-N-[2-(4-methoxyphenyl)ethyl]acetamide, a compound of formula (Yc9); as a white solid; NMR (DMSO-d6, 90 C) 8.4 (s, 1), 7.8 (s, 1), 7.05 (d, 2), 7.0 (s, 1), 6.75 (d, 2), 6.4 (s, 1), 4.1 (s, 2), 3.7 (s, 3), 3.5 (m, 2), 3.25 (m, 2), 3.05 (m, 2), 2.65 (t, 2), 2.3 (s, 3), 1.7 (m, 2) ppm.

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washThe combined ethyl acetate fractions were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (9:1 CH3CN/NH4OH)

Sources & evidence

ORD record
ord-1e4e5de2d2524c908a2129cff2644677
Source dataset
uspto-grants-2005_05
Patent number
US06887865B2

Reaction notes

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