5-Iodo-6-methylpyrimidine-2,4-diamine → 6-Methyl-5-[3-(3,4,5-trimethoxyphenyl)but-1-ynyl]pyrimidine-2,4-diamine

HRID 1968695Notes

Reaction equation

HRID 1968695 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][CH:12]([C:15]1[CH:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=1)[C:13]#[CH:14]>>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:14]#[C:13][CH:12]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH3:11])=[C:4]([CH3:10])[N:3]=1

Participants

3

Reactant 2

HCID 158557925-Iodo-6-methylpyrimidine-2,4-diamineHCID 161103255-(But-3-yn-2-yl)-1,2,3-trimethoxybenzene

Product 1

HCID 161103266-Methyl-5-[3-(3,4,5-trimethoxyphenyl)but-1-ynyl]pyrimidine-2,4-diamineYield 86%

Procedure

2,4-Diamino-5-iodo-6-methylpyrimidine (250 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)-6-methylpyrimidine as a white powder (294 mg, 86%): Rf=0.29 (9:1, CHCl3:MeOH); mp=191-193° C.; 1H NMR (DMSO-d6) δ 6.76 (s, 2H), 6.19 (s, 2H), 4.02 (q, J) 7.1 Hz, 1H), 3.77 (s, 6H), 3.63 (s, 3H), 2.21 (s, 3H), 1.51 (d, J) 7.1 Hz, 3H); 13C NMR (DMSO-d6) δ 167.0, 164.1, 161.0, 152.8, 139.4, 136.0, 104.0, 100.8, 88.6, 76.4, 60.0, 55.8, 32.5, 24.6, 22.5; Anal. (C18H22N4O3) C, H, N.

Sources & evidence

ORD record
ord-f8ec143948c64eafae0a5a0e353aa313
Source dataset
uspto-grants-2013_04
Patent number
US08426432B2

Reaction notes

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