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 1968693Notes

Reaction equation

HRID 1968693 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5](I)=[C:4]([CH3:10])[N:3]=1.[CH3:11][O:12][C:13]1[CH:18]=[C:17]([CH2:19][C:20]#[CH:21])[CH:16]=[C:15]([O:22][CH3:23])[C:14]=1[O:24][CH3:25]>>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:21]#[C:20][CH2:19][C:17]2[CH:16]=[C:15]([O:22][CH3:23])[C:14]([O:24][CH3:25])=[C:13]([O:12][CH3:11])[CH:18]=2)=[C:4]([CH3:10])[N:3]=1

Participants

3

Reactant 2

HCID 152856211,2,3-Trimethoxy-5-(prop-2-yn-1-yl)benzeneHCID 158557925-Iodo-6-methylpyrimidine-2,4-diamine

Product 1

HCID 161103372,4-Diamino-5-(3-(3,4,5-trimethoxyphenyl)prop-1-ynyl)-6-methylpyrimidineYield 85.3%

Procedure

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-bd913f5de70c43e19a06c18fc953e783
Source dataset
uspto-grants-2013_04
Patent number
US08426432B2

Reaction notes

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