2,4,5-Trichloropyrimidine → 5-chloro-N2-(5-cyclopropyl-1,3-oxazol-2-yl)-N4-{2-methoxy-4-[4-(4-methyl-4-oxido-1,4-azaphosphinan-1-yl)piperidin-1-yl]phenyl}pyrimidine-2,4-diamine

HRID 921359Notes

Reaction equation

HRID 921359 reaction equation
COC1C=C(N2CCC(N3CCP(C)(=O)CC3)CC2)C=CC=1N.ClC1N=C(Cl)C(Cl)=CN=1.Cl[C:34]1[N:39]=[C:38]([NH:40][C:41]2[CH:46]=[CH:45][C:44]([N:47]3[CH2:52][CH2:51][CH:50]([N:53]4[CH2:58][CH2:57][P:56]([CH3:60])(=[O:59])[CH2:55][CH2:54]4)[CH2:49][CH2:48]3)=[CH:43][C:42]=2[O:61][CH3:62])[C:37]([Cl:63])=[CH:36][N:35]=1.[CH:64]1([C:67]2[O:71][C:70]([NH2:72])=[N:69][CH:68]=2)[CH2:66][CH2:65]1>>[Cl:63][C:37]1[C:38]([NH:40][C:41]2[CH:46]=[CH:45][C:44]([N:47]3[CH2:48][CH2:49][CH:50]([N:53]4[CH2:58][CH2:57][P:56]([CH3:60])(=[O:59])[CH2:55][CH2:54]4)[CH2:51][CH2:52]3)=[CH:43][C:42]=2[O:61][CH3:62])=[N:39][C:34]([NH:72][C:70]2[O:71][C:67]([CH:64]3[CH2:66][CH2:65]3)=[CH:68][N:69]=2)=[N:35][CH:36]=1

Participants

5

Reactant 4

HCID 2372592,4,5-TrichloropyrimidineHCID 670532735-Cyclopropyl-1,3-oxazol-2-amineHCID 670532902-Methoxy-4-[4-(4-methyl-4-oxido-1,4-azaphosphinan-1-yl)piperidin-1-yl]anilineHCID 866688032,5-dichloro-N-{2-methoxy-4-[4-(4-methyl-4-oxido-1,4-azaphosphinan-1-yl)piperidin-1-yl]phenyl}pyrimidin-4-amine2×

Product 1

HCID 681580175-chloro-N2-(5-cyclopropyl-1,3-oxazol-2-yl)-N4-{2-methoxy-4-[4-(4-methyl-4-oxido-1,4-azaphosphinan-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-methyl-4-oxido-1,4-azaphosphinan-1-yl)piperidin-1-yl]aniline with 2,4,5-trichloropyrimidine to generate 2,5-dichloro-N-{2-methoxy-4-[4-(4-methyl-4-oxido-1,4-azaphosphinan-1-yl)piperidin-1-yl]phenyl}pyrimidin-4-amine. 2,5-dichloro-N-{2-methoxy-4-[4-(4-methyl-4-oxido-1,4-azaphosphinan-1-yl)piperidin-1-yl]phenyl}pyrimidin-4-amine is then reacted with 5-cyclopropyl-1,3-oxazol-2-amine according to the procedure described in Example 32.

Workup

  1. customThis compound can be prepared as in Example 32

Sources & evidence

ORD record
ord-7ad02d1cd89c4f3db6586b3b26255bd2
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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