5-Iodo-6-methylpyrimidine-2,4-diamine → 3-(2,4-Diamino-6-methylpyrimidin-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ol

HRID 1968697Notes

Reaction equation

HRID 1968697 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:14]=[C:15]([CH:23]([OH:26])[C:24]#[CH:25])[CH:16]=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20]>>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:25]#[C:24][CH:23]([C:15]2[CH:16]=[C:17]([O:21][CH3:22])[C:18]([O:19][CH3:20])=[C:13]([O:12][CH3:11])[CH:14]=2)[OH:26])=[C:4]([CH3:10])[N:3]=1

Participants

3

Reactant 2

HCID 158557925-Iodo-6-methylpyrimidine-2,4-diamineHCID 161103271-(3,4,5-Trimethoxyphenyl)-2-propyn-1-ol

Product 1

HCID 161103283-(2,4-Diamino-6-methylpyrimidin-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-olYield 80%

Procedure

2,4-Diamino-5-iodo-6-methylpyrimidine (250 mg) was allowed to react with 1-(3,4,5-Trimethoxyphenyl)prop-2-yn-1-ol (444 mg) as per the general procedure to afford 3-(2,4-Diamino-6-methylpyrimidin-5-yl)-1-(3,4,5-trimethoxyphenyl) prop-2-yn-1-ol as a yellow powder (275 mg, 80%): Rf=0.12 (9:1, CHCl3:MeOH); mp=174-176° C.; 1H NMR (DMSO-d6) δ 6.85 (s, 2H), 6.27 (s, 2H), 5.98 (d, J) 5.6 Hz, 1H), 5.53 (d, J) 5.4 Hz, 1H), 3.78 (s, 6H), 3.65 (s, 3H), 2.19 (s, 3H), 1.51 (d, J) 7.1 Hz, 3H); 13C NMR (DMSO-d6) δ 167.1, 164.3, 161.2, 152.7, 138.3, 136.7, 103.7, 99.1, 87.9, 79.5, 63.6, 60.0, 55.8, 22.5; HRFAB[M+Li]351.1638 (calculated C17H20N4O4Li: 351.1645).

Sources & evidence

ORD record
ord-494d2161c3af4aa69f8902e470f729fa
Source dataset
uspto-grants-2013_04
Patent number
US08426432B2

Reaction notes

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