HCID 22060492, compound → 5-amino-6-ethoxycarbonyl-N2,N4-bis(3-hydroxyphenyl)-2,4-pyrimidinediamine

HRID 2278066Notes

Reaction equation

HRID 2278066 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)[N:9]=[C:8]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=2)[C:7]=1[N+:28]([O-])=O)=[O:5])[CH3:2]>C(O)C.[Pd]>[NH2:28][C:7]1[C:8]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=2)=[N:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)=[N:11][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

4

Reactant 1

HCID 22060492HCID 22060492, compound

Product 1

HCID 220608815-amino-6-ethoxycarbonyl-N2,N4-bis(3-hydroxyphenyl)-2,4-pyrimidinediamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 6-ethoxycarbonyl-N2,N4-bis(3-hydroxyphenyl)-5-nitro-2,4-pyrimidinediamine and 10% Pd/C (10% by weight) in ethanol was prepared and reacted in a Parr bottle under hydrogen gas (20 PSI) for 1 h. The reaction mixture was filtered through Celite. Purification by column chromatography gave 5-amino-6-ethoxycarbonyl-N2,N4-bis(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.30 (bs, 1H), 7.18-7.10 (m, 3H), 7.00 (t, 2H, J=8.1 Hz), 6.59-6.54 (m, 1H), 6.33 (dd, 1H, J=2.1 and 11.1 Hz), 4.39 (q, 2H, J=6.9 Hz), 1.43 (t, 3H, J=6.9 Hz); LCMS: ret. time: 19.24 min.; purity: 100%; MS (m/e): 382 (MH+).

Workup

  1. customwas prepared
  2. customreacted in a Parr bottle under hydrogen gas (20 PSI) for 1 h
  3. filtrationThe reaction mixture was filtered through Celite
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-75b4bc24009d45b1998807629250b84d
Source dataset
uspto-grants-2015_09
Patent number
US09133133B2

Reaction notes

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