2,4,5-Trichloropyrimidine → 5-chloro-N2-[5-(dimethylphosphoryl)-3-methoxypyrazin-2-yl]-N4-{2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidine-2,4-diamine

HRID 921336Notes

Reaction equation

HRID 921336 reaction equation
COC1C=C(N2CCC(N3CCN(C)CC3)CC2)C=CC=1N.ClC1N=C(Cl)C(Cl)=CN=1.Cl[C:33]1[N:38]=[C:37]([NH:39][C:40]2[CH:45]=[CH:44][C:43]([N:46]3[CH2:51][CH2:50][CH:49]([N:52]4[CH2:57][CH2:56][N:55]([CH3:58])[CH2:54][CH2:53]4)[CH2:48][CH2:47]3)=[CH:42][C:41]=2[O:59][CH3:60])[C:36]([Cl:61])=[CH:35][N:34]=1.[CH3:62][P:63]([C:66]1[N:67]=[C:68]([O:73][CH3:74])[C:69]([NH2:72])=[N:70][CH:71]=1)([CH3:65])=[O:64]>>[Cl:61][C:36]1[C:37]([NH:39][C:40]2[CH:45]=[CH:44][C:43]([N:46]3[CH2:51][CH2:50][CH:49]([N:52]4[CH2:57][CH2:56][N:55]([CH3:58])[CH2:54][CH2:53]4)[CH2:48][CH2:47]3)=[CH:42][C:41]=2[O:59][CH3:60])=[N:38][C:33]([NH:72][C:69]2[C:68]([O:73][CH3:74])=[N:67][C:66]([P:63]([CH3:62])([CH3:65])=[O:64])=[CH:71][N:70]=2)=[N:34][CH:35]=1

Participants

5

Reactant 4

HCID 2372592,4,5-TrichloropyrimidineHCID 457899912-Methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)anilineHCID 670526825-(Dimethylphosphoryl)-3-methoxypyrazin-2-amineHCID 866687982,5-dichloro-N-(2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)pyrimidin-4-amine2×

Product 1

HCID 681568495-chloro-N2-[5-(dimethylphosphoryl)-3-methoxypyrazin-2-yl]-N4-{2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidine-2,4-diamine

Procedure

This compound can be prepared as in Example 32 by reacting 2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]aniline with 2,4,5-trichloropyrimidine to generate 2,5-dichloro-N-{2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidin-4-amine. 2,5-dichloro-N-{2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidin-4-amine is then reacted with 5-(dimethylphosphoryl)-3-methoxypyrazin-2-amine (prepared in Example 33) according to the procedure described in Example 32.

Workup

  1. customThis compound can be prepared as in Example 32

Sources & evidence

ORD record
ord-ed7749e4c3e5481f934f5faf29f618d8
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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