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

HRID 1472015Notes

Reaction equation

HRID 1472015 reaction equation
[CH3:1][P:2]([C:5]1[N:6]=[C:7]([O:12][CH3:13])[C:8]([NH2:11])=[N:9][CH:10]=1)([CH3:4])=[O:3].ClC1N=C(Cl)C(Cl)=CN=1.Cl[C:24]1[N:29]=[C:28]([NH:30]C2C(OC)=NC(P(C)(C)=O)=CN=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](N)=[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]([N:11]([C:8]4[C:7]([O:12][CH3:13])=[N:6][C:5]([P:2]([CH3:1])([CH3:4])=[O:3])=[CH:10][N:9]=4)[C:24]4[N:29]=[C:28]([NH2:30])[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 86668800N2-[5-(1,4'-bipiperidin-1'-yl)-1,3,4-thiadiazol-2-yl]-5-chloro-N-[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-6cb1214397d44ab89721e0752feb8a2a
Source dataset
uspto-grants-2015_04
Patent number
US09012462B2

Reaction notes

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