Sodium Nitrite → 7-chloro-3-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ylamine

HRID 1246743Notes

Reaction equation

HRID 1246743 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH:9][CH2:10][C:11]2[C:16]([CH3:17])=[C:15]([O:18][CH3:19])[C:14]([CH3:20])=[CH:13][N:12]=2)[C:3]=1[NH2:21].[N:22]([O-])=O.[Na+]>>[Cl:1][C:2]1[C:3]2[N:21]=[N:22][N:9]([CH2:10][C:11]3[C:16]([CH3:17])=[C:15]([O:18][CH3:19])[C:14]([CH3:20])=[CH:13][N:12]=3)[C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1

Participants

3

Reactant 2

HCID 23668193Sodium NitriteHCID 582786076-chloro-N4-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)pyrimidine-2,4,5-triamine

Product 1

HCID 219061377-chloro-3-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ylamine

Procedure

A solution of 6-chloro-N4-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-pyrimidine-2,4,5-triamine was treated with a cold aqueous solution of NaNO2, following the general procedure 2. HPLC RT was 3.597 min. 1HNMR (CDCl3): δ 8.22 (s, 1H), 7.12 (broad t, 1H), 4.61 (s, 2H), 4.56–4.55 (d, 2H), 3.80 (s, 3H), 3.00 (s, 2H), 2.29 (s, 3H), 2.27 (s, 3H).

Sources & evidence

ORD record
ord-1dd27972f6064733bc880686c38dda3b
Source dataset
uspto-grants-2006_10
Patent number
US07129244B2

Reaction notes

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