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

Diisopropylethylamine → 7-(2-Fluoro-4-methylsulfanyl-phenylamino)-pyrrolo[1,2-c]pyrimidine-6-carboxylic acid methyl ester

HRID 450119
Notes
Print preview

Reaction equation

HRID 450119 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH:4]([CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][N:19]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][C:9]=1[F:16])=O.C(N(C(C)C)CC)(C)C.O(Cl)Cl.[P+5]>O1CCOCC1>[CH3:1][O:2][C:3]([C:4]1[CH:17]=[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][N:19]2[C:5]=1[NH:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][C:9]=1[F:16])=[O:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 67234471N-(2-Fluoro-4-methylsulfanyl-phenyl)-2-pyrimidin-4-ylmethyl-malonamic acid methyl esterHCID 178479711HCID 178479711, compound

Product 1

HCID 672346767-(2-Fluoro-4-methylsulfanyl-phenylamino)-pyrrolo[1,2-c]pyrimidine-6-carboxylic acid methyl esterYield 42.2%

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(2-fluoro-4-methylsulfanyl-phenyl)-2-pyrimidin-4-ylmethyl-malonamic acid methyl ester (2 g, 5.72 mmol) and diisopropylethyl amine (2.9 mL, 17.2 mmol) in dioxane (30 mL) was added phosphorous (V) oxychloride (2.7 mL, 28.6 mmol) and the reaction mixture heated at reflux for 1 hour. The reaction mixture was cooled to 0° C. and quenched with water (10 mL). The reaction mixture was diluted with saturated aqueous sodium bicarbonate solution (20 mL) and extracted with ethyl acetate (3×10 mL). The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 10-20% ethylacetate in cyclohexane) to yield the title compound as a light brown solid (0.80 g, 42%). LCMS (Method B): RT=3.70 min, M+H+=332.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 1 hour
  3. customquenched with water (10 mL)
  4. additionThe reaction mixture was diluted with saturated aqueous sodium bicarbonate solution (20 mL)
  5. extractionextracted with ethyl acetate (3×10 mL)
  6. washThe combined organic fractions were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-045306fa0ec2457085b46f4e35388be4
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08486963B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes