HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

4-Pyridinemethanamine → [7-(3,4-Dimethoxy-phenyl)-imidazo[1,2-c]pyrimidin-5-yl]pyridin-4-ylmethyl-amine

HRID 1072418
Notes
Print preview

Reaction equation

HRID 1072418 reaction equation
Cl[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[N:3]=1.[NH2:21][CH2:22][C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1.C(N(C(C)C)CC)(C)C>CC(O)C>[CH3:20][O:19][C:13]1[CH:12]=[C:11]([C:4]2[N:3]=[C:2]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[N:7]3[CH:8]=[CH:9][N:10]=[C:6]3[CH:5]=2)[CH:16]=[CH:15][C:14]=1[O:17][CH3:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 773174-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 223865465-Chloro-7-(3,4-dimethoxyphenyl)imidazo[1,2-c]pyrimidine

Product 1

HCID 17931866[7-(3,4-Dimethoxy-phenyl)-imidazo[1,2-c]pyrimidin-5-yl]pyridin-4-ylmethyl-amineYield 52.6%

Reagents, catalysts & solvents 1

HCID 3776Isopropanol
Solvent

Conditions

Temperature
90 °C

Procedure

The mixture of 5-chloro-7-(3,4-dimethoxyphenyl)-imidazo[1,2-c]pyrimidine (57.94 mg, 0.2 mmol), 4-aminomethylpyridine (23.79 mg, 0.22 mmol), and diisopropylethylamine (38.78, 0.3 mmol) in 2-propanol was stirred at 90° C. for 20 h, and cooled to room temperature. The solvent was evaporated, and 5 ml of ice water was added. Then the resulting product was extracted with 2×10 ml of ethyl acetate. The combined extract was dried over MgSO4. Then the solvent was evaporated and 2 ml of ether was added. The produced solid was collected by filtration and dried to give pure product (38 mg, 52.6%) of [7-(3,4-dimethoxy-phenyl)-imidazo[1,2-c]pyrimidin-5-yl]pyridin-4-ylmethyl-amine.

Workup

  1. temperaturecooled to room temperature
  2. customThe solvent was evaporated
  3. addition5 ml of ice water was added
  4. extractionThen the resulting product was extracted with 2×10 ml of ethyl acetate
  5. extractionThe combined extract
  6. dry with materialwas dried over MgSO4
  7. customThen the solvent was evaporated
  8. addition2 ml of ether was added
  9. filtrationThe produced solid was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-5ace11e4df714cb885be6f4f3d0af7a1
Source dataset
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06911443B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes