Phosphorus tribromide → 4-(2-(Bromomethyl)-5-chlorothiazolo[4,5-d]pyrimidin-7-yl)morpholine

HRID 1365772Notes

Reaction equation

HRID 1365772 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH2:11]O)=[N:8][C:6]=2[N:7]=1.P(Br)(Br)[Br:20]>C1C=CC=CC=1>[Br:20][CH2:11][C:9]1[S:10][C:5]2[C:4]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[N:3][C:2]([Cl:1])=[N:7][C:6]=2[N:8]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 57685397(5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)methanol

Product 1

HCID 576853964-(2-(Bromomethyl)-5-chlorothiazolo[4,5-d]pyrimidin-7-yl)morpholine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of (5-chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)methanol 56 (100 mg, 0.4 mmol) in benzene (3.0 mL) at 0° C. was added PBr3 (30 ΔL, 0.4 mmol). The reaction was heated at reflux for 1 hour. After cooling to room temperature the reaction was quenched by the addition of water. The aqueous layer was extracted with EtOAc. The combined organics were dried over Na2SO4 and concentrated in vacuo. The crude 4-(2-(bromomethyl)-5-chlorothiazolo[4,5-d]pyrimidin-7-yl)morpholine 57 did not require further purification (x mg, x %). MS (Q1)×(M)+

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 1 hour
  3. customwas quenched by the addition of water
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialThe combined organics were dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurification (x mg, x %)

Sources & evidence

ORD record
ord-676b8f41931d46ab8dfe0799b569829e
Source dataset
uspto-grants-2011_02
Patent number
US07893059B2

Reaction notes

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