Sodium 3-methyl-2,4-dioxo-1-propyl-6-(quinolin-4-ylmethyl)-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate → 5-{4-Hydroxyisoxazolidin-2-ylcarbonyl}-3-methyl-1-propyl-6-(quinolin-4-ylmethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 131573Notes

Reaction equation

HRID 131573 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([C:23]([O-])=[O:24])=[C:10]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]=[CH:15][CH:14]=3)[S:11][C:5]=2[N:4]([CH2:26][CH2:27][CH3:28])[C:3]1=[O:29].[Na+].Cl.[O:32]1[CH2:36][C@@H:35]([OH:37])[CH2:34][NH:33]1>>[OH:37][CH:35]1[CH2:36][O:32][N:33]([C:23]([C:9]2[C:6]3[C:7](=[O:8])[N:2]([CH3:1])[C:3](=[O:29])[N:4]([CH2:26][CH2:27][CH3:28])[C:5]=3[S:11][C:10]=2[CH2:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[CH:15][CH:14]=2)=[O:24])[CH2:34]1

Participants

3

Reactant 2

HCID 23673252Sodium 3-methyl-2,4-dioxo-1-propyl-6-(quinolin-4-ylmethyl)-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylateHCID 66855047(4S)-1,2-oxazolidin-4-ol hydrochloride

Product 1

HCID 688042195-{4-Hydroxyisoxazolidin-2-ylcarbonyl}-3-methyl-1-propyl-6-(quinolin-4-ylmethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Procedure

Prepared as the method of example 1, part g) using the product of step f) and (S)-isoxazolidin-4-ol hydrochloride. δ 1H DMSO 0.84 (3H, td), 1.60 (2H, septet), 3.21 (3H, d), 3.56 (1H, d), 3.73 (3H, m), 3.81 (1H, d), 3.90 (1H, m), 4.61 (2H, dd), 4.79 (1H, s), 5.52 (1H, m), 7.46 (1H, dd), 7.63 (1H, m) 7.79 (1H, m), 8.05 (1H, d), 8.27 (1H, dd), 8.87 (1H, d). MS (APCI) 481.1 (M++H)

Workup

  1. customPrepared as the method of example 1, part g)

Sources & evidence

ORD record
ord-53768e80e2944445846346345f406c5a
Source dataset
uspto-grants-2008_06
Patent number
US07384950B2

Reaction notes

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