(4S)-1,2-oxazolidin-4-ol hydrochloride → 5-[[4-Hydroxyisoxazolidin-2-yl]carbonyl]-3-methyl-6-[7-methyl-1H-indol-3-ylmethyl]-1-(isobutyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 131569Notes

Reaction equation

HRID 131569 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([C:23]([OH:25])=O)=[C:10]([CH2:12][C:13]3[C:21]4[C:16](=[C:17]([CH3:22])[CH:18]=[CH:19][CH:20]=4)[NH:15][CH:14]=3)[S:11][C:5]=2[N:4]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:3]1=[O:30].Cl.[OH:32][C@@H:33]1[CH2:37][O:36][NH:35][CH2:34]1>>[OH:32][CH:33]1[CH2:37][O:36][N:35]([C:23]([C:9]2[C:6]3[C:7](=[O:8])[N:2]([CH3:1])[C:3](=[O:30])[N:4]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:5]=3[S:11][C:10]=2[CH2:12][C:13]2[C:21]3[C:16](=[C:17]([CH3:22])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)=[O:25])[CH2:34]1

Participants

3

Reactant 2

HCID 66855047(4S)-1,2-oxazolidin-4-ol hydrochlorideHCID 688045541,2,3,4-Tetrahydro-3-methyl-6-[7-methyl-1h-indol-3-ylmethyl]-1-(isobutyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylic acid

Product 1

HCID 688050205-[[4-Hydroxyisoxazolidin-2-yl]carbonyl]-3-methyl-6-[7-methyl-1H-indol-3-ylmethyl]-1-(isobutyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Procedure

Prepared using the procedure described in example 1 part g) from the product of step b) and (S)-4-hydroxyisoxazolidine hydrochloride [Example 1 part b] to give the title compound after purification by flash silica chromatography eluting with 0-3% methanol in ethyl acetate and recrystallisation from ethyl acetate:isohexane (9:1). MS (APCI) 497.1 [M+H] δ 1HDMSO 0.81-0.84 (6H,m), 2-2.1 (1H, m), 2.44 (3H, s), 3.2 (3H, s), 3.5-3.9 (6H, 3m), 4.1-4.2 (2H, m), 4.7-4.8 (1H,2m), 5.5 (1H, d), 6.82-6.87 (2H, m), 7.28-7.38 (2H, m), 10.95 (1H, bs)

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-78ee84140380466ab947e75b6b1e2dec
Source dataset
uspto-grants-2008_06
Patent number
US07384950B2

Reaction notes

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