Isopropanol → HCID 86659303, compound

HRID 2283455Notes

Reaction equation

HRID 2283455 reaction equation
[C@:1]12([CH2:11][S:12]([OH:15])(=[O:14])=[O:13])[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:2]2=[O:3].[NH:16]1[CH2:20][CH2:19][C@H:18](/[CH:21]=[CH:22]/[C:23]2[CH:24]=[N:25][CH:26]=[N:27][CH:28]=2)[CH2:17]1.CC(O)C>>[C@:1]12([CH2:11][S:12]([OH:15])(=[O:13])=[O:14])[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:2]2=[O:3].[NH:16]1[CH2:20][CH2:19][C@H:18](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[N:27][CH:26]=[N:25][CH:24]=2)[CH2:17]1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 11528435753015-44-0

Product 1

HCID 86659303HCID 86659303, compoundYield 63.2%

Procedure

(1S)-(+)-10-Camphorsulfonic acid (1.329 g, 5.72 mmol) was added as a solid to a stirring, warm solution of (R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine free base (1.00 g) in 2-propanol (23 mL, 5.70 mmol) in a round-bottomed flask. Upon cooling to ambient temperature, there was no precipitation of solids. The solution was allowed to stand overnight. Gelatinous material containing white solids was observed. After stirring two days, the mixture was diluted with 2-propanol (10.5 mL) because stirring this jelly-like white mass was difficult. After overnight stirring, the resulting white powder was filtered on a Büchner funnel, washed with 2-propanol (5 mL) (NOTE: The solids appeared to have some solubility in 2-propanol) and dried in a vacuum oven (air bleed) at 50° C. for 6 h to give 1.47 g (63.2%) of a white powder, mp 172-173° C. 1H NMR (DMSO-d6) confirms the 1:1 salt stoichiometry. After standing seven days, a second crop of light-beige needles was observed in the crystallization liquors. This material was filtered, washed with 2-propanol (10 mL) and dried in a vacuum oven (air bleed) at 50° C. for 21 h to give 0.245 g of light-beige needles, mp 173-174° C. 1H NMR (DMSO-d6): δ 9.03 (s, 1 H), 8.87 (s, 2H), 6.57 (m, 2H), 3.41 (dd, 1 H) 3.33 (m, 1 H, partially masked by H2O), 3.21 (m, 1 H), 3.10 (m, 1 H), 2.98 (dd, 1 H), 2.89 (d, 1 H, —CH2- of acid moiety, indicating a mono-salt stoichiometry), 2.64 (m, 1 H), 2.41 (d, 1H, —CH2- of acid moiety, indicating a mono-salt stoichiometry), 2.25 (t, 0.5 H), 2.20 (t 0.5 H), 2.15 (m, 1H), 1.93 (t, 1H), 1.82 (m, 3H), 1.28 (m, 2H, —CH2- of acid moiety, indicating a mono-salt stoichiometry), 1.03 (s, 3H, —CH3 of acid moiety, indicating a mono-salt stoichiometry), 0.73 (s, 3H, —CH3 of acid moiety, indicating a mono-salt stoichiometry).

Workup

  1. customno precipitation of solids
  2. additionGelatinous material containing white solids
  3. additionthe mixture was diluted with 2-propanol (10.5 mL)
  4. stirringbecause stirring this jelly-like white mass
  5. stirringAfter overnight stirring
  6. filtrationthe resulting white powder was filtered on a Büchner funnel
  7. washwashed with 2-propanol (5 mL) (NOTE
  8. customdried in a vacuum oven (air bleed) at 50° C. for 6 h

Sources & evidence

ORD record
ord-ce60302737ee4c53b519bb3d3b271821
Source dataset
uspto-grants-2015_09
Patent number
US09145396B2

Reaction notes

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