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

Dimethylformamide → Ethyl (4,6-diamino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl)(methyl)carbamate

HRID 346538
Notes
Print preview

Reaction equation

HRID 346538 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][C:9](=[O:13])[O:10][CH2:11][CH3:12])=[C:6]([NH2:14])[N:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])[N:16]=2)[N:3]=1.[CH3:32]N(C=O)C.[H-].[Na+].IC>O>[NH2:1][C:2]1[C:7]([N:8]([CH3:32])[C:9](=[O:13])[O:10][CH2:11][CH3:12])=[C:6]([NH2:14])[N:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])[N:16]=2)[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 17973412Ethyl 4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinylcarbamate

Product 1

HCID 21081986Ethyl (4,6-diamino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl)(methyl)carbamate

Reagents, catalysts & solvents

1
HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

54 mg (0.13 mmol) of ethyl 4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinylcarbamate from Example 2 are added to 5 ml of DMF, the mixture is cooled to 0° C., and 7.67 mg (0.19 mmol) of sodium hydride are added. Then 18.14 mg (0.13 mmol) of iodomethane are added dropwise, and the mixture is stirred for one hour. The mixture is mixed with water and extracted with dichloromethane. The combined organic phases are dried over magnesium sulphate and concentrated in a rotary evaporator. The residue is purified first by column chromatography (mobile phase: dichloromethane/methanol=10:1) and then by preparative RP-HPLC.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic phases are dried over magnesium sulphate
  3. concentrationconcentrated in a rotary evaporator
  4. customThe residue is purified first by column chromatography (mobile phase: dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-36c8872da63a4eb69d53207af522fe06
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07173037B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes