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

HRID 881229Notes

Reaction equation

HRID 881229 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)=[CH: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[CH:8]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 46180605(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanol

Product 1

HCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of (2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanol 29 (100 mg, 0.4 mmol) in benzene (3.0 mL) at 0° C. was added PBr3 (30 μL, 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 product 30 did not require further purification (115 mg, 94%). MS (Q1) 350 (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 (115 mg, 94%)

Sources & evidence

ORD record
ord-472e805601fb434bb1420288e71c8bd2
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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