Glycine ethyl ester, hydrochloride → 6-ethoxycarbonyl-N2,N4-bis(ethoxycarbonylmethyl)-5-nitro-2,4-pyrimidinediamine

HRID 76516Notes

Reaction equation

HRID 76516 reaction equation
OC1C=C(NC2N=C(NC3C=C[CH:19]=[C:18]([OH:22])C=3)C(F)=CN=2)C=CC=1.Cl[C:25]1[N:30]=[C:29](Cl)[C:28]([N+:32]([O-:34])=[O:33])=[C:27]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[N:26]=1.Cl.[CH2:41]([O:43][C:44](=[O:47])[CH2:45][NH2:46])[CH3:42]>C(N(CC)CC)C>[CH2:41]([O:43][C:44]([CH2:45][NH:46][C:25]1[N:30]=[C:29]([NH:26][CH2:27][C:35]([O:22][CH2:18][CH3:19])=[O:36])[C:28]([N+:32]([O-:34])=[O:33])=[C:27]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[N:26]=1)=[O:47])[CH3:42]

Participants

5

Reactant 3

HCID 2723640Glycine ethyl ester, hydrochlorideHCID 2761044Ethyl 2,6-dichloro-5-nitropyrimidine-4-carboxylateHCID 9904854R-112

Product 1

HCID 220607356-ethoxycarbonyl-N2,N4-bis(ethoxycarbonylmethyl)-5-nitro-2,4-pyrimidinediamine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a manner similar to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, with the addition of triethylamine, 2,4-dichloro-6-ethoxycarbonyl-5-nitropyrimidine and glycine ethyl ester hydrochloride were reacted to yield N2,N4-bis(ethoxycarbonylmethyl)-6-ethoxycarbonyl-5-nitro-2,4-pyrimidinediamine. 1H NMR (CDCl3): mixture of rotamers δ 8.99 and 8.80 (2bs, 1H), 6.22 and 6.00 (2bs, 1H), 4.45 (t, 2H, J=7.2 Hz), 4.31-4.21 (m, 6H), 4.14 (d, 2H, J=5.1 Hz), 1.39 (t, 3H, J=7.2 Hz), 1.34-1.28 (m, 6H); LCMS: ret. time: 26.06 min.; purity: 99%; MS (m/e): 400 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-5a359d3fc3f94331ba4c8d52cc88c31e
Source dataset
uspto-grants-2014_09
Patent number
US08835430B2

Reaction notes

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