2,4,5-Trichloropyrimidine → HCID 68165237, compound

HRID 921354Notes

Reaction equation

CP(C1C=CC(N)=C(S(C(C)C)(=O)=O)C=1)(C)=O.ClC1N=C(Cl)C(Cl)=CN=1.Cl[C:28]1[N:33]=[C:32]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([P:41]([CH3:44])([CH3:43])=[O:42])=[CH:37][C:36]=2[S:45]([CH:48]([CH3:50])[CH3:49])(=[O:47])=[O:46])[C:31]([Cl:51])=[CH:30][N:29]=1.[N:52]1[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=1[N:58]1[CH2:63][CH2:62][N:61]([C:64]2[S:68][C:67]([NH2:69])=[N:66][N:65]=2)[CH2:60][CH2:59]1>>[Cl:51][C:31]1[C:32]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([P:41]([CH3:44])([CH3:43])=[O:42])=[CH:37][C:36]=2[S:45]([CH:48]([CH3:50])[CH3:49])(=[O:47])=[O:46])=[N:33][C:28]([NH:69][C:67]2[S:68][C:64]([N:61]3[CH2:60][CH2:59][N:58]([C:53]4[CH:54]=[CH:55][CH:56]=[CH:57][N:52]=4)[CH2:63][CH2:62]3)=[N:65][N:66]=2)=[N:29][CH:30]=1

Participants

Reactant 4

HCID 2372592,4,5-Trichloropyrimidine

HCID 1500044HCID 1500044, compound

HCID 67052708HCID 67052708, compound

HCID 86668802HCID 86668802, compound2×

Product 1

HCID 68165237HCID 68165237, compound

Procedure

This compound can be prepared as in Example 32 by reacting 4-(dimethylphosphoryl)-2-(propan-2-ylsulfonyl)aniline with 2,4,5-trichloropyrimidine to generate 2,5-dichloro-N-[4-(dimethylphosphoryl)-2-(propan-2-ylsulfonyl)phenyl]pyrimidin-4-amine. 2,5-dichloro-N-[4-(dimethylphosphoryl)-2-(propan-2-ylsulfonyl)phenyl]pyrimidin-4-amine is then reacted with 5-[4-(pyridin-2-yl)piperazin-1-yl]-1,3,4-thiadiazol-2-amine according to the procedure described in Example 32.

Workup

customThis compound can be prepared as in Example 32

Sources & evidence

ORD record: ord-39c39741025949cab4a806c2731ff445
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273077B2

Reaction notes

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