1,2,3-Trimethoxy-5-(prop-2-yn-1-yl)benzene → 2,4-Diamino-5-(3-(3,4,5-trimethoxyphenyl)prop-1-ynyl)-6-methylpyrimidine

HRID 532983Notes

Reaction equation

HRID 532983 reaction equation
NC1N=C(N)C(I)=C(C)N=1.[NH2:11][C:12]1[N:17]=[C:16]([NH2:18])[C:15]([C:19]#[C:20][CH2:21][C:22]2[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=2)=[C:14]([CH3:34])[N:13]=1.COC1C=C(CC#C)C=C(OC)C=1OC>>[NH2:11][C:12]1[N:17]=[C:16]([NH2:18])[C:15]([C:19]#[C:20][CH2:21][C:22]2[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=2)=[C:14]([CH3:34])[N:13]=1

Participants

3

Reactant 2

HCID 152856211,2,3-Trimethoxy-5-(prop-2-yn-1-yl)benzeneHCID 681540302,4-Diamino-5-(3-(3,4,5-trimethoxyphenyl)prop-1-ynyl)-6-methylpyrimidine 2,4-Diamino-5-iodo-6-methylpyrimidine

Product 1

HCID 161103372,4-Diamino-5-(3-(3,4,5-trimethoxyphenyl)prop-1-ynyl)-6-methylpyrimidineYield 197.3%

Procedure

2,4-Diamino-5-(3-(3,4,5-trimethoxyphenyl)prop-1-ynyl)-6-methylpyrimidine 2,4-Diamino-5-iodo-6-methylpyrimidine (250 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)-6-methylpyrimidine as a white powder (280 mg, 85%): Rf=0.31 (9:1, CHCl3:MeOH); mp=164-166° C.; 1H NMR (DMSO-d6) δ 6.72 (s, 2H), 6.42 (s, 2H), 3.85 (s, 2H), 3.76 (s, 6H), 3.63 (s, 3H), 2.24 (s, 3H); 13C NMR (DMSO-d6) δ 165.0, 164.3, 159.7, 152.8, 135.9, 132.8, 105.0, 96.3, 89.3, 75.8, 60.0, 55.8, 25.7, 21.7; HRFAB [M+Li] 335.1679 (calculated C17H20N4O3Li: 335.1695).

Sources & evidence

ORD record
ord-154948dd21ab4a179315ecd86c6806f2
Source dataset
uspto-grants-2014_10
Patent number
US08853228B2

Reaction notes

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