Methanol → Tert-butyl {6-[3-(2-methyl-5-nitro-phenyl)-1-methyl-ureido]-pyrimidin-4-yl}-carbamate

HRID 1038733Notes

Reaction equation

HRID 1038733 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:4]=1.[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:19]=1[N:27]=[C:28]=[O:29].CO>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:19]=1[NH:27][C:28](=[O:29])[N:2]([C:3]1[N:8]=[CH:7][N:6]=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])[CH:4]=1)[CH3:1]

Participants

6

Reactant 3

HCID 887MethanolHCID 2926092-Methyl-5-nitrophenyl isocyanateHCID 86086992tert-butyl (6-Methylamino-pyrimidin-4-yl)-carbamate

Product 1

HCID 86630719Tert-butyl {6-[3-(2-methyl-5-nitro-phenyl)-1-methyl-ureido]-pyrimidin-4-yl}-carbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of tert-butyl (6-Methylamino-pyrimidin-4-yl)-carbamate (240 mg, 1.07 mmol, 1.0 eq.), commercially available 2-methyl-5-nitrophenylisocyanate (210 mg, 1.18 mmol, 1.1 eq.), and DMAP (26 mg, 0.21 mmol, 0.2 eq.) in toluene (10 ml) is stirred at 80° C. for 24 h. After cooling to room temperature methanol (10 ml) is added and the suspension formed is stirred for 10 min at 50° C. The precipitate is filtered off and washed with methanol (2×10 ml). After drying in vacuo an extremely insoluble colorless powder is obtained: HPLC: tR=8.09 min (purity: 85%, gradient A), ESI-MS: 403.5 [MH]+.

Workup

  1. additionis added
  2. customthe suspension formed
  3. filtrationThe precipitate is filtered off
  4. washwashed with methanol (2×10 ml)
  5. customAfter drying in vacuo an extremely insoluble colorless powder
  6. customis obtained

Sources & evidence

ORD record
ord-d8fd9c8067c14d6c96b83c37ed739854
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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