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

Water → (8-Ethyl-7-imino-6-thiophen-3-yl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine

HRID 3224
Notes
Print preview

Reaction equation

HRID 3224 reaction equation
[H-].[Na+].[S:3]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4]1.[CH2:11]([NH:13][C:14]1[C:19]([CH:20]=O)=[CH:18][N:17]=[C:16]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:15]=1)[CH3:12].O>C(OCCO)C>[CH2:11]([N:13]1[C:14]2[N:15]=[C:16]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:17]=[CH:18][C:19]=2[CH:20]=[C:8]([C:5]2[CH:6]=[CH:7][S:3][CH:4]=2)[C:9]1=[NH:10])[CH3:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 837303-ThienylacetonitrileHCID 108240804-Ethylamino-2-phenylamino-pyrimidine-5-carbaldehyde

Product 1

HCID 10736433(8-Ethyl-7-imino-6-thiophen-3-yl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamineYield 78.9%

Reagents, catalysts & solvents 1

HCID 8076
Glycol monoethyl ether
Solvent

Procedure

To a suspension of NaH (60% in mineral oil, 27 mg) in 5 mL of 2-ethoxyethanol was added 3-thiopheneacetonitrile (168 mg, 1.36 mmol). After stirring for 5 minutes at room temperature, 4-ethylamino-2-phenylamino-pyrimidine-5-carbaldehyde (300 mg, 1.24 mmol) was added, and the reaction heated at 120° C. for 2 hours, resulting in a dark brown solution. Upon cooling, the solution was poured into water which caused precipitation. The resulting precipitate was removed by filtration and washed with water. The crude product was purified by flash chromatography, eluting with 5% methanol/methylene chloride, followed by 10% methanol/methylene chloride. Concentration of product fractions yielded 340 mg (78%) of (8-ethyl-7-imino-6-thiophen-3-yl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine; mp 220°-222° C.

Workup

  1. temperaturethe reaction heated at 120° C. for 2 hours
  2. customresulting in a dark brown solution
  3. temperatureUpon cooling
  4. customprecipitation
  5. customThe resulting precipitate was removed by filtration
  6. washwashed with water
  7. customThe crude product was purified by flash chromatography
  8. washeluting with 5% methanol/methylene chloride

Sources & evidence

ORD record
ord-5ac9e9c1c2b44b098f10a1ddc3f11428
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05733914

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes