Sodium Dithionite → 5,6-Diamino-1-[(3-isopropylisoxazol-5-yl)methyl]-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

HRID 912691Notes

Reaction equation

[NH2:1][C:2]1[N:7]([CH2:8][C:9]2[O:13][N:12]=[C:11]([CH:14]([CH3:16])[CH3:15])[CH:10]=2)[C:6](=[S:17])[NH:5][C:4](=[O:18])[CH:3]=1.[N:19]([O-])=O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>>[NH2:19][C:3]1[C:4](=[O:18])[NH:5][C:6](=[S:17])[N:7]([CH2:8][C:9]2[O:13][N:12]=[C:11]([CH:14]([CH3:15])[CH3:16])[CH:10]=2)[C:2]=1[NH2:1]

Participants

Reactant 3

HCID 24489Sodium Dithionite

HCID 23668193Sodium Nitrite

HCID 866311326-Amino-1-[(3-isopropylisoxazol-5-yl)methyl]-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

Product 1

HCID 866311335,6-Diamino-1-[(3-isopropylisoxazol-5-yl)methyl]-2-thioxo-2,3-dihydropyrimidin-4(1H)-oneYield 33.2%

Procedure

The title compound was prepared in accordance with the general method described in Example 12(c) by using 6-amino-1-[(3-isopropylisoxazol-5-yl)methyl]-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (0.20 g, 0.75 mmol, obtained from Example 15(b)), sodium nitrite (0.060 g, 0.83 mmol) and sodium dithionite (0.26 g, 1.5 mmol) giving the title compound (0.070 g, 33% yield). MS (ESI) m/z 282 (M+1).

Workup

customThe title compound was prepared in accordance with the general method

Sources & evidence

ORD record: ord-56df4af995a242d09195feb6411445e0
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026244B2

Reaction notes

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