Acetaldehyde → 4-(2-{4-[3-(Ethyl-pyridin-3-ylmethyl-amino)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

HRID 14782Notes

Reaction equation

HRID 14782 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]2[CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=4)[N:16]=3)[CH:12]=[CH:13][CH:14]=2)[CH:2]=1.[CH:31](=O)[CH3:32]>>[CH2:31]([N:8]([CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH2:22][CH2:23][C:24]3[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=3)[N:16]=2)[CH:12]=[CH:13][CH:14]=1)[CH3:32]

Participants

3

Reactant 2

HCID 177AcetaldehydeHCID 670448754-[2-(4-{3-[(Pyridin-3-ylmethyl)-amino]-phenyl}-pyrimidin-2-ylamino)-ethyl]-phenol

Product 1

HCID 586036034-(2-{4-[3-(Ethyl-pyridin-3-ylmethyl-amino)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

Procedure

Intermediate 25 was coupled with acetaldehyde following procedure E. LC-MS showed the product had the expected M+H+ of 426. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.4 (s, 1H) 8.39 (d, 1H) 8.2 (d, 1H) 7.6 (d, 1H) 7.5 (s, 1H), 7.3 (m, 3H), 7.0 (d, 1H), 6.9 (d 1H), 6.8 (d, 2H), 6.5 (d, 2H), 4.6 (s, 2H), 3.6 (m, 4H), 2.8 (t, 2H), 1.2 (d, 3H).

Sources & evidence

ORD record
ord-5bde7d3dae964baf82f82b1ea0828d6c
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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