Ammonia → 2-[[2-Chloro-5-[[(2,3-difluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-2-methyl-1,3-propanediol

HRID 731528Notes

Reaction equation

N[C:2]1[S:3][C:4]2[C:9]([NH:10][C:11]([CH3:16])([CH2:14][OH:15])[CH2:12][OH:13])=[N:8][C:7]([S:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=3[F:26])=[N:6][C:5]=2[N:27]=1.[ClH:28].N([O-])=O.[Na+].N>O.C(#N)C>[Cl:28][C:2]1[S:3][C:4]2[C:9]([NH:10][C:11]([CH3:16])([CH2:14][OH:15])[CH2:12][OH:13])=[N:8][C:7]([S:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=3[F:26])=[N:6][C:5]=2[N:27]=1

Participants

Conditions

Temperature: 5 °C

Procedure

The product from step (e) (0.485 g) was suspended in conc.HCl (18 ml) which was then cooled to 15° C. A mixture of water (15 ml) and acetonitrile (25 ml) added to give a solution. Cooled to 5° C. and a solution of sodium nitrite (0.162 g) in water (1 ml) added drop-wise. Stirred at 5° C. for several hours then allowed to warm overnight. Solution cooled to −10° C. and neutralized with ammonia, then concentrated in vacuo. The yellow precipitate was collected by filtration and washed with water. Dried in vacuo to give 0.339 g of product. 67% yield.

Workup

additionadded
customto give a solution
temperatureto warm overnight
concentrationconcentrated in vacuo
filtrationThe yellow precipitate was collected by filtration
washwashed with water
customDried in vacuo

Sources & evidence

ORD record: ord-2ee9af07aec14fa49527f6dd0a305c60
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585867B2

Reaction notes

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