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

Participants

Role	Name	HCID	Charge
Reactant	1,2,3-Trimethoxy-5-(prop-2-yn-1-yl)benzene	HCID 15285621	—
Reactant	5-Iodopyrimidine-2,4-diamine	HCID 16110335	—
Product	5-[3-(3,4,5-Trimethoxyphenyl)prop-1-yn-1-yl]pyrimidine-2,4-diamine	HCID 16110323	80%

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08853228B2
Source dataset	uspto-grants-2014_10
ORD ID	ord-e00c50f257984e6b9800af5b4963af57
Source note	uspto-grants-2014_10