Sodium Carbonate → {2,6-Dimethyl-4-[(4-methyl-2-phenyl-pyrimidin-5-ylmethyl)-amino]-phenyl}-carbamic acid propyl ester

HRID 1820150Notes

Reaction equation

HRID 1820150 reaction equation
[CH2:1]([O:4][C:5](=[O:16])[NH:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([NH2:14])=[CH:9][C:8]=1[CH3:15])[CH2:2][CH3:3].[CH3:17][C:18]1[C:23]([CH:24]=O)=[CH:22][N:21]=[C:20]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:19]=1.C([BH3-])#N.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CO.C(O)(=O)C>[CH2:1]([O:4][C:5](=[O:16])[NH:6][C:7]1[C:8]([CH3:15])=[CH:9][C:10]([NH:14][CH2:24][C:23]2[C:18]([CH3:17])=[N:19][C:20]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[N:21][CH:22]=2)=[CH:11][C:12]=1[CH3:13])[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27765114-Methyl-2-phenylpyrimidine-5-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 68707091(4-Amino-2,6-dimethyl-phenyl)-carbamic acid propyl ester

Product 1

HCID 11647099{2,6-Dimethyl-4-[(4-methyl-2-phenyl-pyrimidin-5-ylmethyl)-amino]-phenyl}-carbamic acid propyl esterYield 33%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
170 °C

Procedure

(4-Amino-2,6-dimethyl-phenyl)-carbamic acid propyl ester (22 mg) and 4-methyl-2-phenyl-5-pyrimidinecarbaldehyde (20 mg) were dissolved in methanol (0.5 mL) and heated to 170° C. for 10 minutes in a sealed microwave process vial. Sodium cyanoborohydride (2 M in methanol, 250 uL) and acetic acid (100 uL) were added and the reaction mixture was heated to 50° C. for 2 hours. Aqueous sodium carbonate (10%, 1 mL) was added, the product was extracted with ethyl acetate (2×1 mL), and the combined organic phases were concentrated in vacuo. The crude product was redissolved in dimethyl sulfoxide (0.5 mL) of which 0.25 mL was subjected to preparative LC-MS purification to furnish 6.6 mg (33% yield) of the title compound as an oil. LC-MS (m/z) 405 (MH+); tR=3.12, (UV, ELSD) 84%, 99%.

Workup

  1. temperaturethe reaction mixture was heated to 50° C. for 2 hours
  2. extractionthe product was extracted with ethyl acetate (2×1 mL)
  3. concentrationthe combined organic phases were concentrated in vacuo
  4. dissolutionThe crude product was redissolved in dimethyl sulfoxide (0.5 mL) of which 0.25 mL
  5. customwas subjected to preparative LC-MS purification

Sources & evidence

ORD record
ord-73358e09c08a429e9624d610aa77c1e5
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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