Butylamine → Ethyl 2-((4-((2-amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxy-benzyl)(ethyl)amino)acetate

HRID 2207068Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6](OS(C2C(C)=CC(C)=CC=2C)(=O)=O)[C:5]([CH2:21][C:22]2[CH:37]=[CH:36][C:25]([CH2:26][N:27]([CH2:34][CH3:35])[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:24][C:23]=2[O:38][CH3:39])=[C:4]([CH3:40])[N:3]=1.[CH2:41]([NH2:45])[CH2:42][CH2:43][CH3:44]>>[NH2:1][C:2]1[N:7]=[C:6]([NH:45][CH2:41][CH2:42][CH2:43][CH3:44])[C:5]([CH2:21][C:22]2[CH:37]=[CH:36][C:25]([CH2:26][N:27]([CH2:34][CH3:35])[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:24][C:23]=2[O:38][CH3:39])=[C:4]([CH3:40])[N:3]=1

Participants

Reactant 2

HCID 8007Butylamine

HCID 117992606Ethyl 2-((4-((2-amino-4-(mesitylsulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(ethyl)amino)acetate

Product 1

HCID 117992671Ethyl 2-((4-((2-amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxy-benzyl)(ethyl)amino)acetateYield 66%

Procedure

The sub-title compound was synthesized by the method of example 1 step (viii) from the product of example 1 step (vii) (150 mg) and 1-butylamine (56 mg). The sub-title compound (77 mg) was obtained as a yellow oil; 1H NMR (CDCl3); 6.94 (1H, s), 6.86 (1H, d), 6.77 (1H, d), 4.84 (1H, t), 4.55 (2H, br s), 4.13 (2H, q), 3.88 (3H, s), 3.70 (2H, s), 3.64 (2H, s), 3.30-3.23 (4H, m), 2.66 (2H, q), 2.30 (3H, s), 1.43-1.34 (2H, m), 1.24 (3H, t), 1.19-1.12 (2H, m), 1.06 (3H, t), 0.83 (3H, t).

Sources & evidence

ORD record: ord-a0c25f22f1a24a7189e93770c07335bf
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376398B2

Reaction notes

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