1-(3,4,5-Trimethoxyphenyl)-2-propyn-1-ol → 3-(2,4-Diaminopyrimidin-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ol

Participants

Role	Name	HCID	Charge
Reactant	1-(3,4,5-Trimethoxyphenyl)-2-propyn-1-ol	HCID 16110327	—
Reactant	5-Iodopyrimidine-2,4-diamine	HCID 16110335	—
Product	3-(2,4-Diaminopyrimidin-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ol	HCID 16110339	78%

Reaction Steps

2,4-Diamino-5-iodopyrimidine (236 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-Diaminopyrimidin-5-yl)-1-(3,4,5-trimethoxyphenyl)-prop-2-yn-1-ol as a yellow powder (257 mg, 78%): Rf=0.12 (9:1, CHCl3:MeOH); mp=203-205° C.; 1H NMR (DMSO-d6) δ 7.84 (s, 1H), 6.83 (s, 2H), 6.34 (s, 2H), 6.01 (d, J) 5.6 Hz, 1H), 5.50 (d, J) 5.4 Hz, 1H), 3.78 (s, 6H), 3.65 (s, 3H); 13C NMR (DMSO-d6) δ 163.8, 162.3, 158.2, 152.7, 138.3, 136.7, 109.3, 103.6, 96.3, 79.3, 63.4, 60.0, 55.8; Anal. (C16H18N4O4) C, H, N.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08853228B2
Source dataset	uspto-grants-2014_10
ORD ID	ord-7b37d4eab57346be81a1142ce6ba5a83
Source note	uspto-grants-2014_10