Acetone → 2-(5-Chloro-7-morpholinothiazolo[5,4-d]pyrimidin-2-yl)propan-2-ol

HRID 1692759Notes

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[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.C([N-]C(C)C)(C)C.[Li+].[CH3:25][C:26]([CH3:28])=[O:27].C(Cl)Cl>O1CCCC1.CCCCCCC.O1CCCC1.C(C1C=CC=CC=1)C>[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[N:10]=[C:9]([C:26]([OH:27])([CH3:28])[CH3:25])[S:8][C:6]=2[N:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

4-(5-Chlorothiazolo[5,4-d]pyrimidin-7-yl)morpholine 14 was slurried in tetrahydrofuran and cooled to −78° C. under nitrogen. Two equivalents of 2M lithium diisopropylamide in heptane/tetrahydrofuran/ethylbenzene was added slowly and the solution was stirred for 30 minutes. Acetone (6 eq) was added and the solution was stirred at −78° C. for an additional one hour. Ice was added and the solution was warmed to room temperature before extraction with methylene chloride. The organic layer was dried with sodium sulfate and concentrated. The resulting residue was purified on silica gel to give the light yellow solid of 2-(5-chloro-7-morpholinothiazolo[5,4-d]pyrimidin-2-yl)propan-2-ol 68.

Workup

stirringthe solution was stirred at −78° C. for an additional one hour
additionIce was added
dry with materialThe organic layer was dried with sodium sulfate
concentrationconcentrated
customThe resulting residue was purified on silica gel

Sources & evidence

ORD record: ord-43d90336890b47ebb88e4ddedd57a896
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158626B2

Reaction notes

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