2,4,5-Trichloropyrimidine → N2-[5-(1,4'-bipiperidin-1'-yl)-1,3,4-thiadiazol-2-yl]-5-chloro-N4-[5-(dimethylphosphoryl)-3-methoxypyrazin-2-yl]pyrimidine-2,4-diamine

HRID 921352Notes

Reaction equation

HRID 921352 reaction equation
CP(C1N=C(OC)C(N)=NC=1)(C)=O.ClC1N=C(Cl)C(Cl)=CN=1.Cl[C:24]1[N:29]=[C:28]([NH:30][C:31]2[C:36]([O:37][CH3:38])=[N:35][C:34]([P:39]([CH3:42])([CH3:41])=[O:40])=[CH:33][N:32]=2)[C:27]([Cl:43])=[CH:26][N:25]=1.[N:44]1([CH:50]2[CH2:55][CH2:54][N:53]([C:56]3[S:60][C:59]([NH2:61])=[N:58][N:57]=3)[CH2:52][CH2:51]2)[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]1>>[N:44]1([CH:50]2[CH2:55][CH2:54][N:53]([C:56]3[S:60][C:59]([NH:61][C:24]4[N:29]=[C:28]([NH:30][C:31]5[C:36]([O:37][CH3:38])=[N:35][C:34]([P:39]([CH3:42])([CH3:41])=[O:40])=[CH:33][N:32]=5)[C:27]([Cl:43])=[CH:26][N:25]=4)=[N:58][N:57]=3)[CH2:52][CH2:51]2)[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]1

Participants

5

Reactant 4

HCID 2372592,4,5-TrichloropyrimidineHCID 69172095-(4-Piperidin-1-ylpiperidin-1-yl)-1,3,4-thiadiazol-2-amineHCID 670526825-(Dimethylphosphoryl)-3-methoxypyrazin-2-amineHCID 866688012,5-dichloro-N-[5-(dimethylphosphoryl)-3-methoxypyrazin-2-yl]pyrimidin-4-amine2×

Product 1

HCID 68165236N2-[5-(1,4'-bipiperidin-1'-yl)-1,3,4-thiadiazol-2-yl]-5-chloro-N4-[5-(dimethylphosphoryl)-3-methoxypyrazin-2-yl]pyrimidine-2,4-diamine

Procedure

This compound can be prepared as in Example 32 by reacting 5-(dimethylphosphoryl)-3-methoxypyrazin-2-amine (prepared In example 33) with 2,4,5-trichloropyrimidine to generate 2,5-dichloro-N-[5-(dimethylphosphoryl)-3-methoxypyrazin-2-yl]pyrimidin-4-amine. 2,5-dichloro-N-[5-(dimethylphosphoryl)-3-methoxypyrazin-2-yl]pyrimidin-4-amine is then reacted with 5-(1,4′-bipiperidin-1′-yl)-1,3,4-thiadiazol-2-amine according to the procedure described in Example 321.

Workup

  1. customThis compound can be prepared as in Example 32

Sources & evidence

ORD record
ord-0a33155355274be0aa4b15d1d5180db8
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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