(2-Thienylmethyl)amine → 5-chloro-N4-[2-methoxy-4-(4-methyl-4-oxido-1,4-azaphosphinan-1-yl)phenyl]-N2-(thiophen-2-ylmethyl)pyrimidine-2,4-diamine

HRID 921345Notes

Reaction equation

HRID 921345 reaction equation
COC1C=C(N2CCP(C)(=O)CC2)C=CC=1N.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]([N:41]3[CH2:46][CH2:45][P:44]([CH3:48])(=[O:47])[CH2:43][CH2:42]3)=[CH:37][C:36]=2[O:49][CH3:50])[C:31]([Cl:51])=[CH:30][N:29]=1.[S:52]1[CH:56]=[CH:55][CH:54]=[C:53]1[CH2:57][NH2:58]>>[Cl:51][C:31]1[C:32]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([N:41]3[CH2:46][CH2:45][P:44]([CH3:48])(=[O:47])[CH2:43][CH2:42]3)=[CH:37][C:36]=2[O:49][CH3:50])=[N:33][C:28]([NH:58][CH2:57][C:53]2[S:52][CH:56]=[CH:55][CH:54]=2)=[N:29][CH:30]=1

Participants

5

Reactant 4

HCID 34005(2-Thienylmethyl)amineHCID 2372592,4,5-TrichloropyrimidineHCID 670533272-Methoxy-4-(4-methyl-4-oxido-1,4-azaphosphinan-1-yl)anilineHCID 866687992,5-dichloro-N-[2-methoxy-4-(4-methyl-4-oxido-1,4-azaphosphinan-1-yl)phenyl]pyrimidin-4-amine2×

Product 1

HCID 681573795-chloro-N4-[2-methoxy-4-(4-methyl-4-oxido-1,4-azaphosphinan-1-yl)phenyl]-N2-(thiophen-2-ylmethyl)pyrimidine-2,4-diamine

Procedure

The compound can be prepared as in Example 32 by reacting 2-methoxy-4-(4-methyl-4-oxido-1,4-azaphosphinan-1-yl)aniline with 2,4,5-trichloropyrimidine generating 2,5-dichloro-N-[2-methoxy-4-(4-methyl-4-oxido-1,4-azaphosphinan-1-yl)phenyl]pyrimidin-4-amine. 2,5-dichloro-N-[2-methoxy-4-(4-methyl-4-oxido-1,4-azaphosphinan-1-yl)phenyl]pyrimidin-4-amine is then reacted with 1-(thiophen-2-yl)methanamine as described in Example 32.

Workup

  1. customThe compound can be prepared as in Example 32

Sources & evidence

ORD record
ord-78e68def4c1343c5b73290e57ece6010
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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