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Hydrochloric Acid → 2-[4-Amino-5-(4-phenoxyphenyl)pyrrolo[2,3-d]pyrimidin-7-yl]-2-methylpropionamide

HRID 51501
Notes
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Reaction equation

HRID 51501 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[OH-].[Na+].Br[C:27]([CH3:32])([CH3:31])[C:28]([NH2:30])=[O:29].Cl>CN1CCCN(C)C1=O.O>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:15][CH:16]=3)=[CH:9][N:8]([C:27]([CH3:32])([CH3:31])[C:28]([NH2:30])=[O:29])[C:4]=2[N:5]=[CH:6][N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1012352-Bromo-2-methylpropanamide2×HCID 120422345-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Product 1

HCID 227362342-[4-Amino-5-(4-phenoxyphenyl)pyrrolo[2,3-d]pyrimidin-7-yl]-2-methylpropionamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×
HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

4-Amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine (200 mg) was dissolved in 1,3-dimethyl-3,4,5,6-tetrahydro-2-(1H)-pyrimidinone (1.5 ml) with stirring and sodium hydroxide (0.158 g) was added at ambient temperature and the mixture stirred for 15 minutes. 2-Bromo-2-methylpropanamide (0.5 g) was added and the mixture was stirred vigorously for 18 hours at ambient temperature under a water-free atmosphere, then further 2-bromo-2-methylpropanamide (0.15 g) was added and stirred for a further 24 hours. Water (3 ml) was added to the reaction mixture together with dilute hydrochloric acid (5M) to adjust the pH to 0. The suspension was added to water (60 ml) and the mixture left to stand for 18 hours at ambient temperature. The solid was collected by filtration, washed well with water and dried under high vacuum at 50° C. The solid was purified by preparative HPLC (reverse phase). Appropriate fractions were collected and combined and extracted with dichloromethane. Evaporation of the dichloromethane gave 2-[4-amino-5-(4-phenoxyphenyl)pyrrolo[2,3-d]pyrimidin-7-yl]-2-methylpropionamide, m.p. 227-228° C.

Workup

  1. stirringthe mixture stirred for 15 minutes
  2. stirringthe mixture was stirred vigorously for 18 hours at ambient temperature under a water-free atmosphere
  3. stirringstirred for a further 24 hours
  4. waitthe mixture left
  5. filtrationThe solid was collected by filtration
  6. washwashed well with water
  7. customdried under high vacuum at 50° C
  8. customThe solid was purified by preparative HPLC (reverse phase)
  9. customAppropriate fractions were collected
  10. extractionextracted with dichloromethane
  11. customEvaporation of the dichloromethane

Sources & evidence

ORD record
ord-fd31b76a3bbf4949ac2f97e1e31b5090
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06713474B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes