rel-(2R,6S)-2,6-dimethylpiperazine → HCID 59151328, compound

HRID 2403395Notes

Reaction equation

HRID 2403395 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH:11]=O)=[CH:8][C:6]=2[N:7]=1.[CH3:19][C@H:20]1[CH2:25][NH:24][CH2:23][C@@H:22]([CH3:26])[NH:21]1>>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH2:11][N:24]3[CH2:23][C@H:22]([CH3:26])[NH:21][C@H:20]([CH3:19])[CH2:25]3)=[CH:8][C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 59151328HCID 59151328, compound

Procedure

NMR: (400 Mhz, CDCl3): 1.19-1.24 (6H, m, CH3), 2.61 (2H, t (J 10.72), CH2), 2.80 (3H, s, CH3), 2.88-2.90 (2H, m, CH2), 3.59 (2H, d (J 10.46), CH2), 3.93-4.00 (8H, m, CH2) 4.14 (2H, s, CH2), 7.12 (1H, s, ar), 7.51 (1H, t (J 7.80), ar), 7.60 (1H, d (J 8.29), ar), 8.32 (1H, d (J 6.73), ar), 9.04 (1H, s, ar), 10.10 (1H, b, NH) 6: Reaction between 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde and cis-2,6-dimethyl-piperazine using procedure C yielded 2-chloro-6-((3R,5S)-3,5-dimethyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine. This compound treated with methane sulphonyl chloride using standard conditions to yield 2-chloro-6-((3R,5S)-4-methanesulfonyl-3,5-dimethyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine. This compound was subjected to procedure A to yield the desired final compound which was purified using flash chromatography.

Sources & evidence

ORD record
ord-cb38e1b554ff457e875365a9a7de2a55
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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