Tert-Butylamine → HCID 86594260, compound

HRID 2223139Notes

Reaction equation

HRID 2223139 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:23][C:24]1[C:32]2[C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([NH2:39])[CH:34]=3)=[N:30][C:29]([CH3:40])=[N:28][C:27]=2[S:26][C:25]=1[C:41](O)=[S:42].CCN(C(C)C)C(C)C.[C:53]([NH2:57])([CH3:56])([CH3:55])[CH3:54]>C(Cl)Cl.CN(C=O)C.C(Cl)Cl>[C:53]([NH:57][C:41]([C:25]1[S:26][C:27]2[N:28]=[C:29]([CH3:40])[N:30]=[C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([NH2:39])[CH:34]=3)[C:32]=2[C:24]=1[NH2:23])=[S:42])([CH3:56])([CH3:55])[CH3:54]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178432515HCID 178432515, compound

Product 1

HCID 86594260HCID 86594260, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

TBTU (16.1 g) was added to a solution of 5-amino-4-(3-aminophenyl)-2-methylthio-thieno[2,3-d]pyrimidine-6-carboxylic acid (example 1(f), 14.0 g), DIPEA (17.4 ml) and tert-butylamine (7.3 g) in DCM/DMF (1/1, v/v, 250 ml). After 3 h at room temperature, the mixture was diluted with DCM (50 ml), washed with sat. aq. NaHCO3 (3×100 ml), 0.1 N aq. HCl (100 ml) and water (100 ml). The organic layer was concentrated under reduced pressure. The crude product was purified by crystallisation from warm abs.

Workup

  1. washwashed with sat. aq. NaHCO3 (3×100 ml), 0.1 N aq. HCl (100 ml) and water (100 ml)
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customThe crude product was purified by crystallisation
  4. temperaturefrom warm abs

Sources & evidence

ORD record
ord-67a33e4be9b0493a9a206d9ab8685868
Source dataset
uspto-grants-2008_05
Patent number
US07375109B2

Reaction notes

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