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

HRID 391145Notes

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]

Participants

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

extractionDCM/saturated aqueous NaHCO3 extraction of the cooled mixture

Sources & evidence

ORD record: ord-9b53cd39ca094638bc1f8caa6d8bb65d
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383620B2

Reaction notes

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