Ethylenediamine → N-(2-Amino-ethyl)-3-[(5,7-diamino-pyrimido[4,5-d]pyrimidin-2-yl)-(2-ethoxy-naphthalen-1-ylmethyl)-amino]-2-hydroxy-propionamide

HRID 1393134Notes

Reaction equation

HRID 1393134 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]2[N:9]=[C:10]([N:13]([CH2:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][C:22]=3[O:31][CH2:32][CH3:33])[CH2:14][CH:15]([OH:19])[C:16](O)=[O:17])[N:11]=[CH:12][C:3]=12.CN([P+](Br)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:61]([NH2:64])[CH2:62][NH2:63]>CN(C=O)C>[NH2:63][CH2:62][CH2:61][NH:64][C:16](=[O:17])[CH:15]([OH:19])[CH2:14][N:13]([C:10]1[N:11]=[CH:12][C:3]2[C:4]([N:9]=1)=[N:5][C:6]([NH2:8])=[N:7][C:2]=2[NH2:1])[CH2:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[O:31][CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 81531DiisopropylethylamineHCID 10221847Bromotris(dimethylamino)phosphonium HexafluorophosphateHCID 596793243-[(5,7-Diamino-pyrimido[4,5-d]pyrimidin-2-yl)-(2-ethoxy-naphthalen-1-ylmethyl)-amino]-2-hydroxy-propionic acid

Product 1

HCID 59679346N-(2-Amino-ethyl)-3-[(5,7-diamino-pyrimido[4,5-d]pyrimidin-2-yl)-(2-ethoxy-naphthalen-1-ylmethyl)-amino]-2-hydroxy-propionamideYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-[(5,7-diamino-pyrimido[4,5-d]pyrimidin-2-yl)-(2-ethoxy-naphthalen-1-ylmethyl)-amino]-2-hydroxy-propionic acid (200 mg, 0.445 mmol) in dry DMF (2 ml) was added BroP (249 mg, 0.534 mmol). After the mixture was stirred for 30 min, DIEA (126 mg, 0.979 mmol) was added. After stirring for another 20 min, ethylene diamine (53.5 mg, 0.89 mmol) was added. The mixture was then stirred at room temperature for 16 hours and was directly purified by prep HPLC to yield 35 mg (16%) of the title compound: MS m/z (M+H) 492.

Workup

  1. stirringAfter stirring for another 20 min
  2. stirringThe mixture was then stirred at room temperature for 16 hours
  3. customwas directly purified by prep HPLC

Sources & evidence

ORD record
ord-c2270d2e8036406a806031ffdb643ba3
Source dataset
uspto-grants-2008_03
Patent number
US07345048B2

Reaction notes

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