6-ethoxycarbonyl-N2,N4-bis(ethoxycarbonylmethyl)-5-nitro-2,4-pyrimidinediamine → HCID 22060313, compound

HRID 76677Notes

Reaction equation

HRID 76677 reaction equation
NC1C(NC2C=CC=C(O)C=2)=NC(NC2C=CC=C(O)C=2)=NC=1C(OCC)=O.[CH2:29]([O:31][C:32]([C:34]1[N:39]=[C:38]([NH:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[N:37]=[C:36]([NH:47][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])[C:35]=1[N+:54]([O-])=O)=[O:33])[CH3:30].[H][H]>[Pd]>[NH2:54][C:35]1[C:36]([NH:47][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])=[N:37][C:38]([NH:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=[N:39][C:34]=1[C:32]([O:31][CH2:29][CH3:30])=[O:33]

Participants

5

Reactant 3

HCID 220607356-ethoxycarbonyl-N2,N4-bis(ethoxycarbonylmethyl)-5-nitro-2,4-pyrimidinediamineHCID 220608815-amino-6-ethoxycarbonyl-N2,N4-bis(3-hydroxyphenyl)-2,4-pyrimidinediamineHCID 178418361HCID 178418361, compound

Product 1

HCID 22060313HCID 22060313, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a manner similar to the preparation of 5-amino-6-ethoxycarbonyl-N2,N4-bis(3-hydroxyphenyl)-2,4-pyrimidinediamine, 6-ethoxycarbonyl-N2,N4-bis(ethoxycarbonylmethyl)-5-nitro-2,4-pyrimidinediamine, hydrogen, and 10% Pd/C were reacted to yield 5-amino-N2,N4-bis(ethoxycarbonylmethyl)-6-ethoxycarbonyl-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 6.25 (bs, 2H), 4.38 (q, 2H, J=6.9 Hz), 4.23-4.14 (m, 6H), 4.05 (bs, 2H), 1.39 (t, 3H, J=6.9 Hz), 1.30-1.22 (m, 6H); LCMS: ret. time: 17.67 min.; purity: 95%; MS (m/e): 370 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-5789e984c0fe404982883ed1c4869635
Source dataset
uspto-grants-2014_09
Patent number
US08835430B2

Reaction notes

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