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Trifluoroacetic acid → (S)-3-(2-amino-5-(4-(3-(tert-butyldimethylsilyloxy)propoxy)-2-methoxybenzyl)-6-methylpyrimidin-4-ylamino)hexan-1-ol

HRID 2207091
Notes
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Reaction equation

HRID 2207091 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C@@H:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][OH:12].CC1C=C(C)C=C(C)C=1S(O[C:29]1[C:34]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH2:43][CH2:44][CH2:45][O:46][Si:47]([C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:49])[CH3:48])=[CH:38][C:37]=2[O:54][CH3:55])=[C:33]([CH3:56])[N:32]=[C:31]([NH2:57])[N:30]=1)(=O)=O>C(#N)CC.C(=O)([O-])O.[Na+]>[NH2:57][C:31]1[N:30]=[C:29]([NH:8][C@@H:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][OH:12])[C:34]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH2:43][CH2:44][CH2:45][O:46][Si:47]([C:50]([CH3:51])([CH3:52])[CH3:53])([CH3:49])[CH3:48])=[CH:38][C:37]=2[O:54][CH3:55])=[C:33]([CH3:56])[N:32]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11062353(S)-3-aminohexan-1-olHCID 871670752-Amino-5-(4-(3-(tert-butyldimethylsilyloxy)propoxy)-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate

Product 1

HCID 131735875(S)-3-(2-amino-5-(4-(3-(tert-butyldimethylsilyloxy)propoxy)-2-methoxybenzyl)-6-methylpyrimidin-4-ylamino)hexan-1-olYield 80.7%

Reagents, catalysts & solvents 2

HCID 7854PropionitrileSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
120 °C

Procedure

Trifluoroacetic acid (0.154 mL) was added to the mixture of (S)-3-aminohexan-1-ol (586 mg) and the product from step (i) (616 mg) in propionitrile (6 mL). After the mixture was heated at 120° C. for 23 h, the reaction mixture was cooled to RT, diluted with sat. sodium hydrogen carbonate and extracted with EtOAc. The combined organic layer was dried and concentrated under reduced pressure. The residue was purified by flash column chromatography on amino silica gel to afford the sub-title compound (430 mg) as a colorless oil; 1H NMR (CDCl3); 6.83 (1H, d), 6.44 (1H, d), 6.39 (1H, dd), 4.79 (2H, br s), 4.15-4.04 (1H, m), 4.00 (2H, t), 3.85 (3H, s), 3.77 (2H, t), 3.60 (2H, s), 3.50-3.40 (1H, m), 3.33-3.22 (1H, m), 2.36 (3H, s), 2.00-1.88 (2H, m), 1.86-1.71 (1H, m), 1.48-1.32 (1H, m), 1.30-0.95 (4H, m), 0.86 (9H, s), 0.75 (3H, t), 0.01 (6H, s); LC-MS: m/z 534.

Workup

  1. temperaturethe reaction mixture was cooled to RT
  2. extractionextracted with EtOAc
  3. customThe combined organic layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography on amino silica gel

Sources & evidence

ORD record
ord-cbfccdfe5d6b43639afcbbc9b601e392
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09376398B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes