Methanol → (S)-1-[5-tert-Butyl-3-(4-methyl-furazan-3-ylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol

HRID 2173610Notes

Reaction equation

HRID 2173610 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([N:16]2[CH2:20][CH2:19][C:18](F)(F)[CH2:17]2)[C:8]2[N:13]=[N:12][N:11]([CH2:14][CH3:15])[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].C(C1N=C(N2CCC(F)(F)C2)C2N=NNC=2N=1)(C)(C)C.Br[CH2:44][C:45]1C(C)=[N:48][O:47][N:46]=1.C[OH:52]>>[C:1]([C:5]1[N:6]=[C:7]([N:16]2[CH2:20][CH2:19][C@H:18]([OH:52])[CH2:17]2)[C:8]2[N:13]=[N:12][N:11]([CH2:14][C:15]3[C:45]([CH3:44])=[N:46][O:47][N:48]=3)[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 887MethanolHCID 198327413-(Bromomethyl)-4-methyl-1,2,5-oxadiazoleHCID 715582055-tert-Butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-3-ethyl-3H-[1,2,3]triazolo[4,5-d]pyrimidineHCID 178441789HCID 178441789, compound

Product 1

HCID 86296046(S)-1-[5-tert-Butyl-3-(4-methyl-furazan-3-ylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol

Procedure

In analogy to the procedure described for the synthesis of 5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)-3-ethyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine (example 61), the title compound was prepared from 5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine and 3-(bromomethyl)-4-methyl-1,2,5-oxadiazole. After completion of the substitution reaction methanol was added and the mixture was stirred for 1 h at room temperature and subsequently subjected to purification with preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3. After evaporation of the product containing fractions the title compound was isolated as light-yellow gum. MS(m/e): 359.3 (MH+).

Workup

  1. additionwas added
  2. customsubsequently subjected to purification with preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile, water and NEt3
  5. customAfter evaporation of the product
  6. additioncontaining fractions the title compound
  7. customwas isolated as light-yellow gum

Sources & evidence

ORD record
ord-3ddc0bb1ce9f4b3b9e77c13a9dfa796e
Source dataset
uspto-grants-2015_06
Patent number
US09056866B2

Reaction notes

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