Tetrahydrofuran → (5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)(4-methylsulfonylpiperazin-1-yl)methanone

HRID 1692800Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[S:10][C:9](I)=[N:8][C:6]=2[N:7]=1.C(N(CC)CC)C.Cl.[CH3:26][S:27]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)(=[O:29])=[O:28].[O:36]1CCC[CH2:37]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[S:10][C:9]([C:37]([N:33]3[CH2:34][CH2:35][N:30]([S:27]([CH3:26])(=[O:29])=[O:28])[CH2:31][CH2:32]3)=[O:36])=[N:8][C:6]=2[N:7]=1

Participants

Conditions

Temperature: 55 °C

Procedure

4-(5-Chloro-2-iodothiazolo[4,5-d]pyrimidin-7-yl)morpholine 27 was dissolved in tetrahydrofuran and combined with triethylamine, 1-methylsulfonylpiperazine hydrochloride (2 eq), and trans-dichlorobis(triphenylphosphine)palladium(II) (0.1 eq). The solution was flushed with carbon monoxide stirred under a carbon monoxide balloon at 55° C. overnight. The solution was cooled to room temperature. Water was added and the solution was filtered to yield the tan product of (5-chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)(4-methylsulfonylpiperazin-1-yl)methanone.

Workup

customThe solution was flushed with carbon monoxide
temperatureThe solution was cooled to room temperature
additionWater was added
filtrationthe solution was filtered

Sources & evidence

ORD record: ord-b2c97af3713a4f5481bb3980e9d42407
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158626B2

Reaction notes

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