n-[(2,4-Diaminothieno[2,3-d]pyrimidin-5-yl)methyl]-n,n-diphenylamine → 9-[(2,4-Diaminothieno[2,3-d]pyrimidin-5-yl)methyl]-9,10-dihydrodibenz-[b,f]azepine

HRID 1827718Notes

Reaction equation

HRID 1827718 reaction equation
NC1N=C(N)C2C(CN(C3C=CC=CC=3)C3C=CC=CC=3)=CSC=2N=1.[NH2:26][C:27]1[N:28]=[C:29]([NH2:37])[C:30]2[C:35]([CH3:36])=[CH:34][S:33][C:31]=2[N:32]=1.[CH:38]1[C:48]2[C:42](=[N:43][C:44]3[CH:52]=[CH:51][CH2:50][CH2:49][C:45]=3[CH2:46][CH:47]=2)[CH:41]=[CH:40][CH:39]=1>>[NH2:26][C:27]1[N:28]=[C:29]([NH2:37])[C:30]2[C:35]([CH2:36][CH:49]3[C:45]4[CH2:46][CH:47]=[C:48]5[CH:38]=[CH:39][CH:40]=[CH:41][C:42]5=[N:43][C:44]=4[CH:52]=[CH:51][CH2:50]3)=[CH:34][S:33][C:31]=2[N:32]=1

Participants

4

Reactant 3

HCID 9906281n-[(2,4-Diaminothieno[2,3-d]pyrimidin-5-yl)methyl]-n,n-diphenylamineHCID 12659534Thieno[2,3-d]pyrimidine-2,4-diamine, 5-methyl-HCID 695914299,10-Dihydrodibenz[b,f]azepine

Product 1

HCID 695911749-[(2,4-Diaminothieno[2,3-d]pyrimidin-5-yl)methyl]-9,10-dihydrodibenz-[b,f]azepine

Procedure

9-[(2,4-Diaminothieno[2,3-d]pyrimidin-5-yl)methyl]-9,10-dihydrodibenz-[b,f]azepine (Formula I: Ar=2,4-diaminohieno[2,3-d]pyrimidi-5-yl; W=CH2; X=N; Z=CH2CH2; m=n=0) is prepared similarly to N-[(2,4-diaminothieno[2,3-d]pyrimidin-5-yl)methyl]-N,N-diphenylamine as disclosed in Example 11 above, by using 2,4-diamino-5-methylthieno[2,3-d]pyrimidine (1.3 g, 7.4 mmol) in Step 1 and 9,10-dihydrodibenz[b,f]azepine (158 mg, 0.8 mmol) in Step 3. The final product and its intermediates chromatography.

Sources & evidence

ORD record
ord-486d05742bd04713bd0de5d2b562200a
Source dataset
uspto-grants-2006_06
Patent number
US07056911B1

Reaction notes

Loading…