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Phosphorus tribromide → 4-(6-(Bromomethyl)-2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)morpholine

HRID 391031
Notes
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Reaction equation

HRID 391031 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([CH2:11]O)=[C:8]([CH3:13])[C:6]=2[N:7]=1.P(Br)(Br)[Br:21]>C1(C)C=CC=CC=1>[Br:21][CH2:11][C:9]1[S:10][C:5]2[C:4]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[N:3][C:2]([Cl:1])=[N:7][C:6]=2[C:8]=1[CH3:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 78358255(2-Chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanol

Product 1

HCID 783582564-(6-(Bromomethyl)-2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)morpholine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirring suspension (2-chloro-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-methanol in toluene at 40° C. was added PBr3 and the reaction mixture stirred at 100° C. overnight. DCM/saturated aqueous NaHCO3 extraction of the cooled mixture gave 6-Bromomethyl-2-chloro-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine.

Workup

  1. extractionDCM/saturated aqueous NaHCO3 extraction of the cooled mixture

Sources & evidence

ORD record
ord-55a82a5dcd1b403da73fbc001a35ce85
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08383620B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes