(S)-3-aminohexan-1-ol → (S)-ethyl 2-(N-(4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)acetamido)acetate

HRID 2207079Notes

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:38]=[CH:37][C:25]([CH2:26][N:27]([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:28](=[O:30])[CH3:29])=[CH:24][C:23]=2[O:39][CH3:40])=[C:4]([CH3:41])[N:3]=1.[NH2:42][C@@H:43]([CH2:47][CH2:48][CH3:49])[CH2:44][CH2:45][OH:46]>>[NH2:1][C:2]1[N:7]=[C:6]([NH:42][C@@H:43]([CH2:47][CH2:48][CH3:49])[CH2:44][CH2:45][OH:46])[C:5]([CH2:21][C:22]2[CH:38]=[CH:37][C:25]([CH2:26][N:27]([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:28](=[O:30])[CH3:29])=[CH:24][C:23]=2[O:39][CH3:40])=[C:4]([CH3:41])[N:3]=1

Participants

Reactant 2

HCID 11062353(S)-3-aminohexan-1-ol

HCID 117992603ethyl 2-(N-(4-((2-amino-4-(mesitylsulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)acetamido)acetate

Product 1

HCID 117999101(S)-ethyl 2-(N-(4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)acetamido)acetateYield 23.8%

Procedure

The sub-title compound was synthesized by the method of example 1 step (viii) from the product of step (ii) (25 mg) and (S)-3-aminohexan-1-ol (15 mg). The sub-title compound (5.1 mg) was obtained as a colourless gum; 1H NMR (CDCl3); 6.93 (1H, d), 6.72-6.67 (2H, m), 4.82 (2H, br s), 4.65 (1H, d), 4.56 (2H, s), 4.18-4.08 (3H, m), 3.99 (2H, s), 3.88 (3H, s), 3.65 (2H, s), 3.48-3.42 (1H, m), 3.32-3.26 (1H, m), 2.33 (3H, s), 2.17 (3H, s), 1.84-1.74 (1H, m), 1.46-1.35 (1H, m), 1.23 (3H, t), 1.16-0.97 (4H, m), 0.73 (3H, t); LC-MS: m/z=502.

Sources & evidence

ORD record: ord-6f91de61907c47248c9f3b92a75712f3
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376398B2

Reaction notes

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