5-Iodopyrimidine-2,4-diamine → 2,4-Diamino-5-(3-methoxy-3-(3,4,5-trimethoxyphenyl)prop-1-ynyl)pyrimidine

HRID 532989Notes

Reaction equation

HRID 532989 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5](I)=[CH:4][N:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[C:16]([CH:18]([O:21][CH3:22])[C:19]#[CH:20])[CH:15]=[C:14]([O:23][CH3:24])[C:13]=1[O:25][CH3:26]>>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:20]#[C:19][CH:18]([O:21][CH3:22])[C:16]2[CH:15]=[C:14]([O:23][CH3:24])[C:13]([O:25][CH3:26])=[C:12]([O:11][CH3:10])[CH:17]=2)=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 161103355-Iodopyrimidine-2,4-diamineHCID 161103401,2,3-Trimethoxy-5-(1-methoxyprop-2-ynyl)benzene

Product 1

HCID 161103292,4-Diamino-5-(3-methoxy-3-(3,4,5-trimethoxyphenyl)prop-1-ynyl)pyrimidineYield 90%

Procedure

2,4-Diamino-5-iodopyrimidine (236 mg) was allowed to react with 1,2,3-Trimethoxy-5-(1-methoxyprop-2-ynyl)benzene (473 mg) as per the general procedure to afford 2,4-Diamino-5-(3-methoxy-3-(3,4,5-trimethoxyphenyl)prop-1-ynyl)pyrimidine as an orange powder (310 mg, 90%): Rf=0.31 (9:1, CHCl3:MeOH); mp=184-186° C.; 1H NMR (DMSO-d6) δ 7.91 (s, 1H), 6.82 (s, 2H), 6.40 (s, 2H), 5.30 (s, 1H), 3.79 (s, 6H), 3.66 (s, 3H), 3.35 (s, 3H); 13C NMR (DMSO-d6) δ 163.8, 162.3, 159.7, 152.8, 137.2, 134.8, 104.6, 92.6, 89.1, 81.9, 73.0, 60.0, 55.9, 55.4; Anal. (C17H20N4O4) C, H, N.

Sources & evidence

ORD record
ord-e131d9b6e98b4aa08ce2108eff4fa876
Source dataset
uspto-grants-2014_10
Patent number
US08853228B2

Reaction notes

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