Bromoform → 2-[[2-Bromo-5-[(phenylmethyl)thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-2-methyl-1-propanol

HRID 1006487Notes

Reaction equation

N[C:2]1[S:3][C:4]2[C:9]([NH:10][C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])=[N:8][C:7]([S:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:6][C:5]=2[N:24]=1.C(ON=O)CC(C)C.C(Br)(Br)[Br:34]>>[Br:34][C:2]1[S:3][C:4]2[C:9]([NH:10][C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])=[N:8][C:7]([S:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:6][C:5]=2[N:24]=1

Participants

Reactant 3

HCID 5558Bromoform

HCID 8053Isoamyl Nitrite

HCID 222884672-[[2-Amino-5-[(phenylmethyl)thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-2-methyl-1-propanol

Product 1

HCID 226491452-[[2-Bromo-5-[(phenylmethyl)thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-2-methyl-1-propanol

Conditions

Temperature: 60 °C

Procedure

To a solution of the product from example 1 step d) (0.1 g) in bromoform (5 ml) was added isoamylnitrite (0.13 ml) and the mixture heated at 60° C. for 10 mins. The mixture was evaporated to dryness and purified (SiO2, ethyl acetate:dichloromethane 1:9 as eluant) to give the subtitle compound as a colourless solid (0.043 g).

Workup

customThe mixture was evaporated to dryness
custompurified (SiO2, ethyl acetate:dichloromethane 1:9 as eluant)

Sources & evidence

ORD record: ord-388776f8a4444cc38b078d50d9d5d35b
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06790850B1

Reaction notes

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