1,2,3-Trimethoxy-5-(prop-2-yn-1-yl)benzene → 5-[3-(3,4,5-Trimethoxyphenyl)prop-1-yn-1-yl]pyrimidine-2,4-diamine

HRID 532981Notes

Reaction equation

HRID 532981 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5](I)=[CH:4][N:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[C:16]([CH2:18][C:19]#[CH:20])[CH:15]=[C:14]([O:21][CH3:22])[C:13]=1[O:23][CH3:24]>>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:20]#[C:19][CH2:18][C:16]2[CH:15]=[C:14]([O:21][CH3:22])[C:13]([O:23][CH3:24])=[C:12]([O:11][CH3:10])[CH:17]=2)=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 152856211,2,3-Trimethoxy-5-(prop-2-yn-1-yl)benzeneHCID 161103355-Iodopyrimidine-2,4-diamine

Product 1

HCID 161103235-[3-(3,4,5-Trimethoxyphenyl)prop-1-yn-1-yl]pyrimidine-2,4-diamineYield 80%

Procedure

2,4-Diamino-5-iodopyrimidine (236 mg) was allowed to react with 1,2,3-Trimethoxy-5-(prop-2-ynyl)benzene (412 mg) as per the general procedure to afford 2,4-Diamino-5-(3-(3,4,5-trimethoxyphenyl)prop-1-ynyl)pyrimidine as a white powder (251 mg, 80%): Rf=0.23 (9:1, CHCl3:MeOH); mp=decomposed above 190° C.; 1H NMR (DMSO-d6) δ 7.84 (s, 1H), 6.71 (s, 2H), 6.26 (s, 2H), 3.80 (s, 2H), 3.77 (s, 6H), 3.63 (s, 3H); 13C NMR (DMSO-d6) δ 163.8, 162.2, 158.7 152.8, 136.0, 132.8, 105.2, 93.1, 90.1 76.5, 60.1, 55.8, 25.6; Anal. (C16H18N4O3) C, H, N.

Sources & evidence

ORD record
ord-e00c50f257984e6b9800af5b4963af57
Source dataset
uspto-grants-2014_10
Patent number
US08853228B2

Reaction notes

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