5-(But-3-yn-2-yl)-1,2,3-trimethoxybenzene → 2,4-Diamino-5-(3-(3,4,5-trimethoxyphenyl)but-1-ynyl)pyrimidine

HRID 532984Notes

Reaction equation

HRID 532984 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5](I)=[CH:4][N:3]=1.[CH3:10][CH:11]([C:14]1[CH:15]=[C:16]([O:24][CH3:25])[C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=1)[C:12]#[CH:13]>>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:13]#[C:12][CH:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=2)[CH3:10])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 161103255-(But-3-yn-2-yl)-1,2,3-trimethoxybenzeneHCID 161103355-Iodopyrimidine-2,4-diamine

Product 1

HCID 161103382,4-Diamino-5-(3-(3,4,5-trimethoxyphenyl)but-1-ynyl)pyrimidineYield 90%

Procedure

2,4-Diamino-5-iodopyrimidine (236 mg) was allowed to react with 5-(But-3-yn-2-yl)-1,2,3-trimethoxybenzene (440 mg) as per the general procedure to afford 2,4-Diamino-5-(3-(3,4,5-trimethoxyphenyl)but-1-ynyl)pyrimidine as a yellow powder (295 mg, 90%): Rf=0.29 (9:1, CHCl3:MeOH); mp=220-222° C.; 1H NMR (DMSO-d6) δ 7.85 (s, 1H), 6.75 (s, 2H), 6.28 (s, 2H), 3.99 (q, J) 6.8 Hz, 1H), 3.78 (s, 6H), 3.63 (s, 3H), 1.50 (d, J) 7.1 Hz, 3H); 13C NMR (DMSO-d6) δ 163.7, 152.8, 139.3, 136.0, 104.2, 104.1, 97.9, 76.2, 60.0, 60.0, 55.9, 55.8, 32.3, 24.3; Anal. (C17H20N4O3) C, H, N.

Sources & evidence

ORD record
ord-c745a98144d44c35abc46821fe760570
Source dataset
uspto-grants-2014_10
Patent number
US08853228B2

Reaction notes

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