Iodine → 4-(5-Chloro-2-iodothiazolo[4,5-d]pyrimidin-7-yl)morpholine

HRID 1692799Notes

Reaction equation

HRID 1692799 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[S:10][CH:9]=[N:8][C:6]=2[N:7]=1.[I:17]I.C[Si]([N-][Si](C)(C)C)(C)C.[K+].O>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[C:5]2[S:10][C:9]([I:17])=[N:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 3251421Potassium bis(trimethylsilyl)amideHCID 576854145-Chloro-7-(morpholin-4-yl)[1,3]thiazolo[4,5-d]pyrimidine

Product 1

HCID 252527634-(5-Chloro-2-iodothiazolo[4,5-d]pyrimidin-7-yl)morpholine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

4-(5-Chlorothiazolo[4,5-d]pyrimidin-7-yl)morpholine 16 was dissolved in tetrahydrofuran and iodine (3 eq) was added. The solution was cooled to −50° C. and potassium bis(trimethylsilyl)amide (1.2 eq of 0.5M solution in toluene) was added over a period of 10 minutes. The solution was warmed to room temperature and stirred overnight. Water was added to quench the reaction and the tetrahydrofuran was removed in vacuo. The residue was brought up in methylene chloride, washed with saturated sodium bicarbonate solution and dried with magnesium sulfate. The solution was concentrated a purified by silica gel chromatography to yield 4-(5-chloro-2-iodothiazolo[4,5-d]pyrimidin-7-yl)morpholine 27.

Workup

  1. temperatureThe solution was warmed to room temperature
  2. customto quench
  3. customthe reaction
  4. customthe tetrahydrofuran was removed in vacuo
  5. washwashed with saturated sodium bicarbonate solution
  6. dry with materialdried with magnesium sulfate
  7. concentrationThe solution was concentrated
  8. customa purified by silica gel chromatography

Sources & evidence

ORD record
ord-9d9fc718f09f49e19176dd53a527d3c2
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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